Agricultural sulfonamides

ABSTRACT

N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted in the 2-position by a carboxy radical, ester, thioester, or amide thereof; e.g. N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide or N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide; are useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.

BACKGROUND OF THE INVENTION

This invention relates to novel N-(heterocyclicaminocarbonyl)arylsulfonamides in which the aryl radical is substituted by a carboxyl radical, ester, thioester or amide thereof. The compounds of this invention and their agriculturally suitable salts, are useful as agricultural chemicals, e.g. plant growth regulants and herbicides.

Netherlands Pat. No. 121,788, published September 15, 1966, discloses the preparation of compounds of the following Formula and their use as general or selective herbicides: ##STR1## wherein R₁ and R₂ may independently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms.

U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2## wherein R₁ is hydrogen or lower saturated aliphatic acyl and

R₂ is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl.

The disclosed compounds are said to provide control of crabgrass, cress, endive, clover and Poa annua.

French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides as being useful as antidiabetic agents: ##STR3## wherein R=H, halogen, CF₃ or alkyl.

Logemann et al. Chem Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR4## wherein R is butyl, phenyl, or ##STR5## and R₁ is hydrogen or methyl.

When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm 19, p. 121-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR6## Based upon similarity to a known compound, the author speculated that the foregoing compound might have a hypoglycemic activity.

Substituted-pyrimidinyl sulfonylureas of the following formula, which are also para-substituted on the phenyl ring, are disclosed in Farmco Ed. Sci., 12, 586 (1957) [Chem. Ab., 53, 18052 g (1959)]: ##STR7## wherein R=H or CH₃.

The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing loss of a portion of such valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency. A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need still exists however, for more effective herbicides.

SUMMARY OF THE INVENTION

According to this invention, there are provided novel compounds of Formula I and their agriculturally suitable salts, e.g. Na, K, alkyl ammonium, trichloroacetic acid, suitable agricultural compositions containing them and methods of using them as herbicides and as plant growth regulants. ##STR8## wherein Q is O, S or ##STR9## when Q is O or S then R is C₁ -C₁₂ alkyl, C₃ -C₁₀ alkenyl; C₃ -C₁₀ alkynyl; C₂ -C₆ alkyl substituted with one to four substituents selected from 0-3 atoms of F, Cl, Br, 0-2 methoxy groups and 0-1 cyano groups; --CH₂ CN; ##STR10## where R₇ ' is H or CH₃ ; C₃ -C₆ alkenyl substituted with 1-3 atoms of F, Cl, Br; C₃ -C₆ alkynyl substituted with one of F, Cl or Br; C₅ -C₈ cycloalkyl; C₅ -C₈ cycloalkenyl; C₅ -C₆ cycloalkyl substituted with OCH₃, alkyl of C₂ -C₄, F, Cl or Br or one to four methyl groups; C₄ -C₁₀ cycloalkylalkyl; C₄ -C₈ cycloalkylalkyl with 1-2 CH₃ ; C₇ -C₁₀ bicycloalkyl; C₇ -C₁₀ bicycloalkenyl; C₁₀ tricycloalkyl, C₁₀ tricycloalkenyl; ##STR11## where R₉ is C₁ -C₃ alkyl or hydrogen, R₁₀ and R₁₁ are independently hydrogen, C₁ -C₃ alkyl, Cl, Br, --OCH₃, --OC₂ H₅ or R₁₀ and R₁₁ may be taken together to form a 5 or 6 member ring: ##STR12## and n is 0, 1, 2 or 3 provided the total number of carbon atoms is ≦12; ##STR13## A is O, S; A₁ is O, S, SO₂ ;

when Q is O, then R is H, M, --CH₂ CH₂ OR₇ ; ##STR14## --CH₂ CH₂ CH₂ OR₇, ##STR15## where R₇ is --CH₂ CH₃, --CH(CH₃)₂, phenyl, --CH₂ CH₂ Cl, --CH₂ CCl₃ ; CH₂ OR₈ ' where R₈ ' is --CH₃, --CH₃ CH₂, --CH(CH₃)₂, --CH₂ CH₂ Cl, --CH₂ CCl₃, phenyl, ##STR16## --CH₂ CH₂ OCH₃, --CH₂ CH₂ OCH₂ CH₃ ; --CH₂ CH₂ O)_(n') R₈, where R₈ is --CH₃, --CH₂ CH₃, --CH(CH₃)₂, phenyl, --CH₂ CH₂ Cl, --CH₂ CCl₃ and n' is 2 or 3; ##STR17## where R₁₂ is --CH₃, --CH₂ CH₃, --CH(CH₃)₂, or phenyl; and

provided R has a total number of carbon atoms ≦13;

when Q is ##STR18## then R is hydrogen; C₁ -C₁₂ alkyl; --CH₂ CH₂ O--_(n'") R₁₂, --CH₂ CH₂ CH₂ OR₁₂ where R₁₂ is as defined above and n'" is 1-3; C₃ -C₁₀ alkenyl; C₃ -C₆ alkynyl; C₃ -C₈ cycloalkyl; C₅ -C₆ cycloalkenyl; C₅ -C₈ cycloalkyl substituted with 1 to 3 substituents selected from 0-2 --OCH₃, 0-3 --CH₃ or --C₂ H₅ ; trifluoromethylcyclohexyl; C₄ -C₁₀ cycloalkylalkyl; C₄ -C₈ cycloalkylalkyl substituted with 1-2 --CH₃ ; --CH₂ CN; --CH₂ CH₂ CN; ##STR19## where n, R₉, R₁₀ and R₁₁ are as defined above; ##STR20## where R' is hydrogen, C₁ -C₄ alkyl, --OCH₃, F, Br, Cl, --CF₃, CN, NO₂, --SO₂ CH₃, --SCH₃, --N(CH₃)₂ ; R" is hydrogen, C₁ -C₄ alkyl, --OCH₃, F, Br, Cl; R'" is hydrogen, --CH₃, Cl, F or Br;

R₆ is hydrogen, C₁ -C₆ alkyl, allyl, --CH₂ CN; or --CH₂ CH₂ CN; or R₆ and R can be taken together to form --(CH₂)₄ --, --(CH₂)₅ --, --(CH₂)₆ --, --CH₂ CH₂ OCH₂ CH₂ --; ##STR21## with the proviso that when R is --OCH₃ or --OC₂ H₅ then R₆ is H or --CH₃ ; when R₆ is --CH₂ CH₂ CN or --CH₂ CN then R is --CH₂ CH₂ CN or CH₂ CN; and R and R₆ have a total number of carbon atoms ≦13; and further provided that when QR is other than ##STR22## then R₂ must be NCO, ##STR23## CF₃ SO₂ NH or CH₃ SO₂ NH; ##STR24## R₂ is H, Cl, Br, F, C₁ -C₃ alkyl, --NO₂, --SO₂ CH₃, --OCH₃, --SCH₃, --CF₃, --N(CH₃)₂, --NH₂, --CN, --NCO, ##STR25## CF₃ SO₂ NH or CH₃ SO₂ NH; B is C₁ -C₄ alkyl optionally substituted with 1-3 atoms of F, Cl, Br or a single OCH₃ group; C₂ -C₄ alkenyl;

B^(I) is C₁ -C₄ alkyl or C₃ -C₄ alkenyl;

B^(II) is C₁ -C₄ alkyl optionally substituted with CH₃ OCH₂ CH₂, CH₃ CH₂ OCH₂ CH₂ or 1-3 atoms of F, Cl or Br; C₃ -C₄ alkenyl;

B^(III) is C₁ -C₄ alkyl optionally substituted with Cl or OCH₃ ; C₃ -C₄ alkenyl;

R₃ is H, Cl, Br, F or CH₃ ;

R₄ is H, or --CH₃ ;

R₅ is H, --CH₃, or --OCH₃ ;

M is an alkali metal;

W is oxygen or sulfur;

X is H, Cl, --CH₃, --OCH₃, --OCH₂ CH₃, --OCH₂ CH₂ OCH₃, CH₂ OCH₃ or CH₂ OCH₂ CH₃ ;

Y is H; F; Cl; Br; C₁ -C₄ alkyl; ##STR26## C₁ -C₄ alkyl substituted with --OCH₃, --OC₂ H₅, --CN, ##STR27## or 1 to 3 atoms of F, Cl, Br; C₃ -C₄ alkenyl; --CH₂ C.tbd.CR₁₃ where R₁₃ is H, --CH₃, --CH₂ Cl; --A--(CH₂)_(n') A₁ --(C₁ -C₃ alkyl), and n', A and A₁ are as previously defined; ##STR28## where L is --NH₂, OH, ##STR29## --NH(C₁ -C₄ alkyl), --N(C₁ -C₄ alkyl)₂, C₁ -C₆ alkoxy; --SCN; --N₃ ; NR₁₆ R₁₇ where R₁₆ is H or CH₃ and R₁₇ is H, --OCH₃, C₁ -C₆ alkyl, C₁ -C₄ alkyl substituted with --CN, ##STR30## C₃ -C₄ alkenyl; C₃ -C₆ cycloalkyl; or C₂ -C₃ alkyl substituted with --OCH₃, OC₂ H₅ ; or R₁₆ and R₁₇ can be taken together to form --CH₂ CH₂ CH₂ CH₂ --, --CH₂ CH₂ OCH₂ CH₂ --; --O--R₁₄ where R₁₄ is C₁ -C₄ alkyl; C₂ -C₄ alkyl substituted with 1-3 atoms of F, Cl or Br; C₁ -C₄ alkyl substituted with cyano; C₃ -C₄ alkenyl, --CH₂ C.tbd.CR₁₃ ; where R₁₃ is as previously defined; ##STR31## --SR₁₅ where R₁₅ is C₁ -C₄ alkyl, C₁ -C₂ alkyl substituted with CN, allyl, propargyl; with the provision that when Y is ≦4 carbon atoms, R is ≦4 carbon atoms, when X is Cl, then Y is Cl, and when X and Y are both H, then R is ≦4 carbon atoms. Z is N or CH;

Y₁ is H, --OCH₃, --CH₃ or OCH₂ CH₃ ;

X₁ is H, Cl, --OCH₃, --OCH₂ CH₃, --CH₃ ; providing that X₁ and Y₁ are not both simultaneously hydrogen and when R₁ is ##STR32## then R₄ and R₅ are both H and R is ≦5 carbon atoms.

Preferred for higher activity and/or lower cost and/or greater ease at synthesis are:

1. Compounds of the generic scope in which W is O; R₃, R₄ and R₅ are H; R₂ is --NCO, ##STR33## CF₃ SO₂ NH or CH₃ SO₂ NH; and Q is O;

2. Compounds of the generic scope in which W is O; R₃, R₄ and R₅ are H; and QR is ##STR34##

3. Compounds of the generic scope in which W is O; R₃, R₄ and R₅ are H; and QR is ##STR35##

4. Compounds of the generic scope in which W is O; R₃ R₄ and R₅ are H; and QR is ##STR36##

More preferred for reasons of even higher activity and/or even lower cost and/or even greater ease of synthesis are:

5. Compounds of preferred 1 in which R₂ is in the 5-position of the benzene ring;

6. Compounds of preferred 1 in which R₁ is ##STR37##

7. Compounds of preferred 6 in which R₂ is in the 5-position at the benzene ring;

8. Compounds of preferred 7 where R is C₁ -C₄ alkyl, C₃ -C₄ alkenyl; C₂ -C₃ alkyl substituted with Cl; CH₂ CH₂ --O--CH₃, CH₂ CH₃); ##STR38## or CH₂ CH₂ CH₂ --O--CH₃, CH₂ CH₃);

9. Compounds of preferred 8 in which X is CH₃, OCH₃, or CH₂ OCH₃ ;

10. Compounds of preferred 9 in which Y is CH₃, CH₃ CH₂, C₁ -C₄ alkoxy or CH₃ S;

11. Compounds of preferred 10 in which Y is CH₃, CH₃ O, or SCH₃ ;

12. Compounds of preferred 11 in which R is CH₃ ;

13. Compounds of preferred 11 in which B, B^(I), B^(II) are C₁ -C₄ alkyl and B^(III) is C₁ -C₄ alkyl optionally substituted with an atom of F, Cl or Br;

14. Compounds of preferred 13 in which X and Y are independently CH₃ or CH₃ O;

15. Compounds of preferred 14 in which R is CH₃ ;

16. Compounds of preferred 15 in which R₂ is ##STR39##

Also more preferred for reasons of even higher activity and/or even lower cost and/or even greater ease of synthesis are:

17. Compounds of preferred 2 in which R₂ is H, F, Cl, Br, CH₃, CH₃ O or CF₃ ;

18. Compounds of preferred 17 in which R₁ is ##STR40##

19. Compounds of preferred 18 in which X is CH₃, CH₃ O, or CH₂ OCH₃ ; and Y is CH₃, CH₃ O or CH₃ S;

20. Compounds of preferred 19 in which R₂ is H; X and Y are independently CH₃ or CH₃ O.

21. Compounds of preferred 20 in which QR is ##STR41##

Also more preferred and in increasing order for reasons of even higher activity and/or even lower cost and/or even greater ease of synthesis are:

22. Compounds of preferred 3 in which R₂ is H, F, Cl, Br, CH₃, CH₃ O or CF₃ ;

23. Compounds of preferred 22 in which R₁ is ##STR42##

24. Compounds of preferred 23 in which X and Y are independently CH₃ or CH₃ O;

25. Compounds of preferred 24 in which R₂ is H;

Specifically preferred for reasons of highest activity and/or lowest cost and/or greatest ease of synthesis are:

Methyl 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-5-[(methylamino)carbonylamino]benzoate;

Methyl 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-5-[(methylamino)carbonylamino]benzoate;

Methyl 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-5-[(methylamino)carbonylamino]benzoate;

Methyl 5-[(1,1-dimethylethylamino)carbonylamino]-2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

Methyl 5-[(1,1-dimethylethylamino)carbonylamino]-2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

Methyl 5-[(1,1-dimethylethylamino)carbonylamino]-2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

Methyl 5-[(1-methylethylamino)carbonylamino]-2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminosulfonyl]benzoate;

Methyl 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-4-[(methylamino)carbonylamino]benzoate;

Methyl 4-(acetylamino)-2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

Methyl 4-[(2-chloroethylamino)carbonylamino]-2-[[(4,6-dimethoxypyrimidin-2-yl)aminosulfonyl]benzoate;

1-[2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzooyl]-2,3-dihydro-1H-indole;

1-[2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]-2,3-dihydro-1H-indole;

1-[2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]-2,3-dihydro-1H-indole;

1-[2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]-2,3-dihydro-1H-indole;

1-[2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]-2,3-dihydro-1H-indole;

1-[2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]-2,3-dihydro-1H-indole;

2-oxiranylmethyl 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

2-oxiranylmethyl 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

2-oxiranylmethyl 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

2-oxiranylmethyl 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

2-oxiranylmethyl 2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

2-oxiranylmethyl 2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate;

2-oxiranylmethyl 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate; and

Methyl 2-[[(4-methoxymethyl-6-methylthio-1,3,5-triazin-2yl)aminocarbonyl]aminosulfonyl]benzoate.

SYNTHESIS

Many of the compounds of Formula I where QR is ##STR43## can be prepared from the corresponding esters by reaction with the dialkylaluminum-N-alkyl-amide derivatives according to Equation 1. ##STR44##

The intermediate alkylaminoaluminum compounds prepared according to A. Basha, M. Lipton and S. W. Weinreb, Tetrahedron Letters, 4171 (1977), are comingled with a suspension of the esters in methylene chloride and the mixture is refluxed for 12 to 24 hours. The product can be isolated by addition of aqueous hydrochloric acid to decompose the residual reaction mass and the product is dissolved in the methylene chloride. Evaporation of the methylene chloride yields the desired product which may be purified by crystallization or column chromatography.

The preparation of esters of Formula II is described in European patent application No. 7687.

Compounds of Formula IV, which are useful intermediates in Equation 3, are prepared as shown in Equation 2. ##STR45##

The conditions described for Equation 1 are suitable for the conversion of the esters of Formula III to the amides IV as shown in Equation 2.

The amides of Formula IV are especially useful for the preparation of compounds of Formula I wherein Y has an ester substituent CO₂ (C₁ -C₆), by the route described in Equation 3. ##STR46##

The procedure of Equation 3 and the preparation of the heterocyclic isothiocyanates which are used in Equation 3 are described in European Patent Application No. 7687.

As shown in Equation 4, compounds of Formula I can be prepared by the reaction of an appropriately substituted sulfonyl N-methylcarbonyl chloride or sulfonyl N-methylthiocarbonyl chloride of Formula VII with an appropriate aminopyrimidine or aminotriazine of Formula VIII. ##STR47##

The procedure of Equation 4 and the preparation of the chlorides of Formula VII are described in European Patent Application No. 7687.

Compounds wherein R is ##STR48## can be prepared by the reaction of salts of the parent acid (R=H) with the corresponding halogen compounds as shown in Equation 5. ##STR49##

The procedure of Equation 5 and the preparation of compounds of Formula X are described in European Patent Application No. 7687.

Compounds of Formula I wherein R₂ is isocyanate can be prepared by combining an appropriate 2-aminopyrimidine or 2-aminotriazine with an appropriately substituted isocyanatobenzenesulfonyl isocyanate. ##STR50##

The compounds of Formula XII can be prepared from the corresponding o-carbonyl substituted aminobenzenesulfonamide by the action of phosgene as shown in Equation 7. ##STR51##

The procedures of Equations 6 and 7 are described in European Patent Application No. 1515.

The isocyanate substituent in compound XIII can be converted readily to the carbamates (XIIIa), thiolcarbamates (XIIIb), or urea derivatives (XIIIc) of this invention by reaction thereof respectively with the appropriate alcohol (Equation 8), thiol (Equation 9) or amine (Equation 10). ##STR52##

The reactions of Equations 8, 9 and 10 can be carried out in situ with isocyanate compound (XIII), or isocyanate compound (XIII) can first be isolated and added to the alcohol, thiol or amine neat or in a non-reactive solvent. In any event, the reactions of Equations 8, 9 and 10 proceed readily and are mildly exothermic; however, in some cases, the addition of a catalyst such as dibutyl tin dilaurate or 1,4-diazabicyclooctane may be used.

Alternative procedures of preparation of compounds XIIa, XIIb and XIIc respectively from the appropriate chlorocarbonate, chlorothiocarbonate and isocyanate is described in European Patent Application No. 1515.

Compounds of Formula I in which R₂ is ##STR53## HNO₂ SCF₃ or --HNO₂ SCH₃ are prepared from the corresponding amino compound. The amino substituent in compound XIV can be converted readily to the amide (XIVa) or sulfonamide (XIVb) of this invention by reaction thereof respectively with the appropriate acid chloride (Equation 11) or sulfonyl chloride (Equation 12). ##STR54##

Compounds of Formula XIV can be prepared from the corresponding nitro compounds by catalytic hydrogenation as shown in Equation 13. ##STR55##

The procedures of Equations 11, 12 and 13 are described in European Patent Application No. 1515.

The synthesis of heterocyclic amines has been reviewed in "The Chemistry of Heterocyclic Compounds" a series published by Interscience Publ., New York and London. 2-Aminopyrimidines are described by D. J. Brown in "The Pyrimidines", Vol. XVI of this series. The 2-amino-1,3,5-triazines are reviewed by K. R. Huffman and in "The Triazines" of this same series. The synthesis of triazines are also described by F. C. Schaefer, U.S. Pat. No. 3,154,547 and K. R. Huffman and F. C. Schaeffer, J. Org. Chem. 28, 1816-1821 (1963).

The preparation of agriculturally suitable salts of the compounds of Formula I, as well as starting materials and intermediates for said compounds, not otherwise described herein, is disclosed in my application Ser. Nos. 824,805, filed August 15, 1977 and 840,389, filed October 6, 1977, the contents of which are incorporated herein by reference.

The compounds of this invention and their preparation are further illustrated by the following examples wherein temperatures are given in degrees centigrade and parts by weight unless otherwise indicated.

EXAMPLE 1 1-{2-{[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoyl}-2,3-dihydro-1H-indole

To 1.44 g of trimethylaluminum in 100 ml of methylene chloride was added 2.4 g of indoline with stirring at ambient temperature. To this mixture was added 3.0 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and the solution refluxed for 18 hours. The reaction mixture was treated with aqueous hydrochloric acid and the precipitated product (0.7 g) was found to be pure by thin layer chromatography (TLC) on silica gel with an eluting solvent of ethyl acetate and hexane, 1:1; m.p. 224°-225° C.; IR: 3200 cm⁻¹ NH, 1740 cm⁻¹ sulfonylurea carbonyl, 1640 cm⁻¹ amide carbonyl.

NMR: in trifluoroacetic acid-D, 3.1 ppm, T, 2H, methylene next to nitrogen in indoline ring, 4.1 ppm S, 6H, OCH₃ on pyrimidine ring, 6.3 ppm S, 1H, pyrimidine hydrogen in position 5, methylene of indoline ring next to aromatic ring under OCH₃ peak, 7.2-8.6 ppm, M, 8H, aromatic.

EXAMPLE 2 Methyl 2-{[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl}-5-[(1,1-dimethylethylamino)carbonylamino]benzoate

To 0.5 g of methyl 4-amino-2-{[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoate in 50 ml of methylene chloride was added 4 ml of t-butyl isocyanate. The solution was stirred at ambient temperature for 18 hours. Evaporation of solvent and chromatography of the residue on silica gel with CH₂ Cl₂ /hexane 1:1 as eluents gave 0.1 g of pure product, m.p. 186°-8° C. IR, 3400 cm⁻¹ NH, 1730 cm⁻¹ and 1680 cm⁻¹ sulfonylurea carbonyl and urea carbonyl. NMR, 1.4 ppm, t-butyl-, S; 3.9 ppm OCH₃ of ester, S; 4.0 ppm, OCH₃ of pyrimidine, S; 5.8 ppm, CH of pyrimidine ring, S; 7.6-8.3 ppm, aromatic protons, M.

EXAMPLE 3 2-Oxiranylmethyl 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate

To 1.75 g of 2-(4,6-dimethoxypyrimidin-2-yl-aminocarbonylsulfonyl)benzoic acid is added 0.51 g of triethylamine in 10 ml of tetrahydrofuran and 0.48 g of epichlorohydrin in 10 ml of tetrahydrofuran. The mixture is heated to reflux for 1.5 hours, filtered, and the tetrahydrofuran evaporated in vacuo. The residue is dissolved in ethyl acetate and washed with water and aqueous sodium bicarbinate. The organic phase was dried over magnesium sulfate, filtered and the solvent evaporated in vacuo. The resultant product is recrystallized from a methylene chloride and 1-chlorobutane mixture.

EXAMPLE 4 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-ethoxyaminocarbonylbenzenesulfonamide

To 2.9 g of trimethylaluminum in 100 ml of methylene chloride is added 2.0 g of ethoxyamine hydrochloride with stirring at ambient temperature. To this mixture is added 3.0 g of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide and the solution is refluxed for 18 hours. The reaction mixture is treated with aqueous hydrochloric acid and the resulting precipitated product is purified by chromatography.

EXAMPLE 5 2-Methoxycarbonyl-5-isocyanato-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide

To 27 g of 2-methoxycarbonyl-5-isocyanatobenzenesulfonylisocyanate in 250 ml of anhydrous acetonitrile is added in small portions at ambient temperatures, 14 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine, the mixture is then stirred at ambient temperature for 16 hours. The resultant product, a white precipitate is removed by filtration and dried in vacuo.

EXAMPLE 6 Methyl 2-[[(4-methoxymethyl-6-methylthio-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate

To a solution of 0.8 g of 4-methoxymethyl-6-methylthio-2-amino-1,3,5-triazine in 15 ml of anhydrous methylene chloride was added 1.5 g of 2-methoxycarbonylbenzenesulfonylisocyanate. The mixture was heated for one hour and then stirred at ambient temperature for 18 hours. Solvent was removed in vacuo and the residue was triturated with 1-chlorobutane (50 ml) and filtered to give 1.7 g of the desired product, m.p. 147°-149° C. mmr: 2.6 ppm δ, 3H; 3.4 ppm δ, 3H; 3.85 ppm δ, 3H; 4.45 δ, 2H; 7.65-8.5 broad, 4H.

EXAMPLE 7 4-Methoxymethyl-6-methylthio-2-amino-1,3,5-triazine

Methoxyacetonitrile (35.5 g), sodium methoxide (25 g) and methanol (250 ml) were stirred at ambient temperature for 18 hours. Ammonium chloride (30 g) was added and the mixture stirred for one hour. The solvent was removed and the residue triturated with ether (150 ml) and then redissolved in methanol (250 ml). Sodium methoxide (26 g) in methanol (250 ml) was added to the mixture which was then rapidly filtered. The filtrate was added to dimethyl N-cyanocarbonimidodithioate (73 g) with stirring. After 3 hours of stirring at ambient temperature the solvent was removed and the residue washed with water and 1-chlorobutane. The solid (45 g) was an equal mixture of the desired methylthio compound and the corresponding methoxy compound. Isolation of the desired methylthio compound was achieved by preparative liquid chromatography (20 g). m.p. 134°-136° C. mmγ (DMSO-d₆) 2.4 ppm δ, 3H; 3.3 ppm δ, 3H; 4.14 ppm δ, 2 H.

By application of one or more of the procedures of Examples 1-7 and/or the methods described above, with the appropriate reactants, the compounds of Tables I to VIII can be prepared.

                                      TABLE I                                      __________________________________________________________________________      ##STR56##                                                                                                                  m.p.                              QR      R.sub.2                                                                              R.sub.3                                                                            W R.sub.5                                                                           X        Y            (°C.)                      __________________________________________________________________________      ##STR57##                                                                             H     H   O H  CH.sub.3 H                                               ##STR58##                                                                             5-F   H   O H  H        Cl                                              ##STR59##                                                                             5-Cl  H   O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR60##                                                                             5-Br  H   O H  CH.sub.3 OCH.sub.3                                       ##STR61##                                                                             5-NO.sub.2                                                                           H   O H  CH.sub.3 OCH.sub.3                                       ##STR62##                                                                             5-OCH.sub.3                                                                          H   O H  CH.sub.3 OCH.sub.3                                       ##STR63##                                                                             5-CH.sub.3                                                                           H   O H  CH.sub.3 CH.sub.3                                        ##STR64##                                                                             5- .sub.-i-C.sub.3 H.sub.7                                                           H   O H  CH.sub.3 OC.sub.2 H.sub.5                                ##STR65##                                                                             5-SCH.sub.3                                                                          H   O H  CH.sub.3 OCH.sub.3                                       ##STR66##                                                                             5-Cl  3-Cl                                                                               O H  CH.sub.3 OCH.sub.3                                       ##STR67##                                                                             5-Cl  3-CH.sub.3                                                                         O H  CH.sub.3 OCH.sub.3                                       ##STR68##                                                                             5-F   3-Cl                                                                               O H  CH.sub.3 OCH.sub.3                                       ##STR69##                                                                             5-NO.sub.2                                                                           3-Cl                                                                               O H  CH.sub.3 OCH.sub.3                                       ##STR70##                                                                             5-Br  3-Br                                                                               O H  CH.sub.3 OCH.sub.3                                       ##STR71##                                                                             6-Cl  H   S H  CH.sub.3 CH.sub.2 OCH.sub.3                              ##STR72##                                                                             H     H   O H  CH.sub.3 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5             ##STR73##                                                                             H     H   O H  CH.sub.3 OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3           ##STR74##                                                                             H     H   O H  CH.sub.3 OCH(CH.sub.3)CO.sub.2 CH.sub.3                  ##STR75##                                                                             H     H   O H  CH.sub.3 OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3            ##STR76##                                                                             H     H   O H  CH.sub.3 OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5              ##STR77##                                                                             H     H   O CH.sub.3                                                                          OCH.sub.3                                                                               OCH.sub.3                                       ##STR78##                                                                             H     H   O CH.sub.3                                                                          OCH.sub.3                                                                               OCH.sub.3                                       ##STR79##                                                                             5-Cl  H   O CH.sub.3                                                                          OCH.sub.3                                                                               CH.sub.3                                        ##STR80##                                                                             6-Cl  H   O CH.sub.3                                                                          OCH.sub.3                                                                               OC.sub.2 H.sub.5                                ##STR81##                                                                             3-CH.sub.3                                                                           H   O CH.sub.3                                                                          OCH.sub.3                                                                               OCH.sub.3                                       ##STR82##                                                                             H     H   O H  CH.sub.3 SCH.sub.2 COOCH.sub.3                           ##STR83##                                                                             H     H   O H  CH.sub.3 S(CH.sub.2).sub.2 OC.sub.2 H.sub.5              ##STR84##                                                                             H     H   O H  CH.sub.3 S(CH.sub.2).sub.2 COOC.sub.2 H.sub.5            ##STR85##                                                                             H     H   O H  CH.sub.3 CH.sub.3                                        ##STR86##                                                                             H     H   O H  CH.sub.3 OCH.sub.3                                       ##STR87##                                                                             H     H   O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR88##                                                                             H     H   O H  CH.sub.3                                                                                 ##STR89##                                      ##STR90##                                                                             H     H   O H  CH.sub.3 OCH.sub.2 CO.sub.2 C.sub.2 H.sub.5              ##STR91##                                                                             H     H   O H  CH.sub.3 SCH.sub.2 CO.sub.2 C.sub.2 H.sub.5              ##STR92##                                                                             H     H   O H  CH.sub.3 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5             ##STR93##                                                                             H     H   O H  CH.sub.3 SCH.sub.2 CH.sub.2 SCH.sub.3                    ##STR94##                                                                             H     H   O H  CH.sub.3                                                                                 ##STR95##                                      ##STR96##                                                                             H     H   O H  CH.sub.3 SCH.sub.2 CH.sub.3                              ##STR97##                                                                             H     H   O H  CH.sub.3 SCH.sub.2 CCH                                   ##STR98##                                                                             5-CF.sub.3                                                                           H   O H  CH.sub.3 OCH.sub.3                                       ##STR99##                                                                             5-N(CH.sub.3).sub.2                                                                  H   O H  CH.sub.3 OCH.sub.3                                       ##STR100##                                                                            5-SO.sub.2 CH.sub.3                                                                  H   O H  CH.sub.3 OCH.sub.3                                       ##STR101##                                                                            5-CN  H   O H  CH.sub.3 OCH.sub.3                                       ##STR102##                                                                            5-NH.sub.2                                                                           H   O H  CH.sub.3 OCH.sub.3                                       ##STR103##                                                                            4-Cl  5-Cl                                                                               O H  OCH.sub.3                                                                               CH.sub.3                                        ##STR104##                                                                            4-Cl  5-Cl                                                                               O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR105##                                                                            4-F   H   O H  OCH.sub.3                                                                               CH.sub.3                                        ##STR106##                                                                            4-Br  H   O H  OCH.sub.3                                                                               CH.sub.3                                        ##STR107##                                                                            H     H   O H  CH.sub.3 OCH.sub.2 CF.sub.3                              ##STR108##                                                                            H     H   O H  CH.sub.3                                                                                 ##STR109##                                     ##STR110##                                                                            H     H   O H  CH.sub.3 OCH.sub.2 CO.sub.2 CH.sub.3                     ##STR111##                                                                            H     H   O H  CH.sub.3 CH.sub.2 OCH.sub.3                              ##STR112##                                                                            H     H   O CH.sub.3                                                                          CH.sub.3 CH.sub.3                                        ##STR113##                                                                            H     H   O H  OCH.sub.2 CH.sub.2 OCH.sub.3                                                            OCH.sub.2 CH.sub.2 OCH.sub.3                    ##STR114##                                                                            H     H   O H  OCH.sub.3                                                                                -n-C.sub.4 H.sub.9                             ##STR115##                                                                            H     H   O H  OCH.sub.3                                                                               CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3            ##STR116##                                                                            H     H   O H  OCH.sub.3                                                                               CH.sub.2 CH.sub.2 CN                            ##STR117##                                                                            H     H   O H  OCH.sub.3                                                                               CH.sub.2 CO.sub.2 CH.sub.3                      ##STR118##                                                                            H     H   O H  OCH.sub.3                                                                               CCl.sub.3                                       ##STR119##                                                                            H     H   O H  OCH.sub.3                                                                                ##STR120##                                     ##STR121##                                                                            H     H   O H  CH.sub.3 (CH.sub.2).sub.3 CH.sub.2 Cl                    ##STR122##                                                                            H     H   O H  OCH.sub.3                                                                               CH.sub.2 CCCH.sub.3                             ##STR123##                                                                            H     H   O H  OCH.sub.3                                                                               CH.sub.2 CCCH.sub.2 Cl                          ##STR124##                                                                            H     H   O H  OCH.sub.3                                                                               NH -n-C.sub.4 H.sub.9                           ##STR125##                                                                            H     H   O H  OCH.sub.3                                                                                ##STR126##                                     ##STR127##                                                                            H     H   O H  OCH.sub.3                                                                                ##STR128##                                     ##STR129##                                                                            H     H   O H  OCH.sub.3                                                                               NH(CH.sub.2).sub.2 CO.sub.2 CH.sub.3            ##STR130##                                                                            H     H   O H  CH.sub.3                                                                                 ##STR131##                                     ##STR132##                                                                            H     H   O H  OCH.sub.3                                                                                ##STR133##                                     ##STR134##                                                                            H     H   O H  CH.sub.3 O(CH.sub.2).sub.3 CH.sub.3                      ##STR135##                                                                            H     H   O H  CH.sub.3 OCH.sub.2 CH.sub.2 Br                           ##STR136##                                                                            H     H   O H  CH.sub.3 OCH.sub.2 CCl.sub.3                             ##STR137##                                                                            H     H   O H  CH.sub.3 OCH.sub.2 CH.sub.2 CH.sub.2 CN                  ##STR138##                                                                            H     H   O H  CH.sub.3 OCH.sub.2 CHCH.sub.2                            ##STR139##                                                                            H     H   O H  CH.sub.3 CH.sub.3                                        ##STR140##                                                                            H     H   O H  CH.sub.3 OCH.sub.3                                       ##STR141##                                                                            H     H   O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR142##                                                                            5-NO.sub.2                                                                           H   O H  CH.sub.3 CH.sub.3                                        ##STR143##                                                                            5-NO.sub. 2                                                                          H   O H  CH.sub.3 OCH.sub.3                                       ##STR144##                                                                            5-NO.sub.2                                                                           H   O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR145##                                                                            5-NH.sub.2                                                                           H   O H  CH.sub.3 OCH.sub.3                                       ##STR146##                                                                            5-NH.sub.2                                                                           H   O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR147##                                                                            5-NH.sub.2                                                                           H   O H  CH.sub.3 CH.sub.3                                        ##STR148##                                                                            5-Cl  H   O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR149##                                                                            5-Cl  H   O H  OCH.sub.3                                                                               CH.sub.3                                        ##STR150##                                                                            5-Cl  H   O H  CH.sub.3 CH.sub.3                                        ##STR151##                                                                            H     H   O H  OCH.sub.2 CH.sub.3                                                                      OCH.sub.2 CH.sub.3                              ##STR152##                                                                            H     H   O H  OCH.sub.3                                                                               OCH.sub.3    224-225°                    ##STR153##                                                                            H     H   O H  CH.sub.3 OCH.sub.3                                       ##STR154##                                                                            H     H   O H  CH.sub.3 CH.sub.3                                        ##STR155##                                                                            H     H   O H  CH.sub.3 CH.sub.3                                        ##STR156##                                                                            5-Cl  H   O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR157##                                                                            4-Cl  Cl  O H  CH.sub.3 OCH.sub.3                                       ##STR158##                                                                            H     H   O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR159##                                                                            5-NO.sub.2                                                                           H   O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR160##                                                                            5-CF.sub.3                                                                           H   O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR161##                                                                            5-SO.sub.2 CH.sub.3                                                                  H   O H  OCH.sub.3                                                                               CH.sub.3                                        ##STR162##                                                                            5-Cl  H   O H  CH.sub.3 CH.sub.3                                        ##STR163##                                                                            H     H   O H  OCH.sub.3                                                                               OCH.sub.3                                       ##STR164##                                                                            H     H   O H  OCH.sub.3                                                                               CH.sub.3                                        ##STR165##                                                                            5-NH.sub.2                                                                           H   O H  OCH.sub.3                                                                               CH.sub.2 OCH.sub.3                              ##STR166##                                                                            5-NH.sub.2                                                                           H   O H  CH.sub.3 OCH.sub.2 CO.sub.2 CH.sub.3                     ##STR167##                                                                            H     H   O H  CH.sub.3 F                                               ##STR168##                                                                            H     H   O H  CH.sub.3 Br                                              ##STR169##                                                                            H     H   O H  CH.sub.3 CO.sub.2 CH.sub.3                               ##STR170##                                                                            H     H   O H  OCH.sub.3                                                                               CH.sub.2 CO.sub.2 CH.sub.3                      ##STR171##                                                                            H     H   O H  OCH.sub.3                                                                               CH.sub.2 CO.sub.2 H                             ##STR172##                                                                            H     H   O H  OCH.sub.3                                                                               CH.sub.2 CO.sub.2 -n-C.sub.4 H.sub.9            ##STR173##                                                                            H     H   O H  OCH.sub.3                                                                               (CH.sub.2).sub.3 CO.sub.2 .sub.-i-C.sub.3                                      H.sub.7                                         ##STR174##                                                                            H     H   O H  OCH.sub.3                                                                               CH.sub.2 CO.sub.2 -n-C.sub.6 H.sub.13           ##STR175##                                                                            H     H   O H  CH.sub.3 NH(CH.sub.2).sub.2 CO.sub.2 .sub.-i-C.sub.                                     3 H.sub.7                                       ##STR176##                                                                            H     H   O H  CH.sub.3                                                                                 ##STR177##                                     ##STR178##                                                                            H     H   O H  CH.sub.3                                                                                 ##STR179##                                     ##STR180##                                                                            H     H   O H  CH.sub.3                                                                                 ##STR181##                                     ##STR182##                                                                            H     H   O H  CH.sub.3                                                                                 ##STR183##                                     ##STR184##                                                                            H     H   O H  CH.sub.3                                                                                 ##STR185##                                     ##STR186##                                                                            H     H   O H  CH.sub.3                                                                                 ##STR187##                                    __________________________________________________________________________

                                      TABLE II                                     __________________________________________________________________________      ##STR188##                                                                                                                   m.p.                            QR      R.sub.2                                                                              R.sub.3                                                                           W R.sub.4                                                                           R.sub.5                                                                           X         Y           (°C.)                    __________________________________________________________________________      ##STR189##                                                                            H     H  O H  H  CH.sub.3  CH.sub.3                                     ##STR190##                                                                            H     H  O H  CH.sub.3                                                                          OCH.sub.3 OCH.sub.3                                    ##STR191##                                                                            H     H  O H  H  H         H                                            ##STR192##                                                                            H     H  S H  H  CH.sub.3  OCH.sub.3                                    ##STR193##                                                                            3-Cl  H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR194##                                                                            3-CH.sub.3                                                                           H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR195##                                                                            3-Cl  5-Cl                                                                              O H  H  OC.sub.2 H.sub.5                                                                         OCH.sub.3                                    ##STR196##                                                                            5-NO.sub.2                                                                           H  O H  H  OC.sub.2 H.sub.5                                                                         OCH.sub.3 CH.sub.2 OCH.sub.3                 ##STR197##                                                                            H     H  O H  H  OCH.sub.3 OCH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3        ##STR198##                                                                            3-Cl  6-Cl                                                                              O H  H  CH.sub.3 CH.sub.2 O                                                                      CH.sub.3 O                                   ##STR199##                                                                            H     H  O H  H  CH.sub.3 O                                                                               CF.sub.3                                     ##STR200##                                                                            3-OCH.sub.3                                                                          H  S H  H  CH.sub.3  OC.sub.2 H.sub.5                             ##STR201##                                                                            5-SCH.sub.3                                                                          H  O H  H  CH.sub.3  O(CH.sub.2).sub.2 OC.sub.2 H.sub.5           ##STR202##                                                                            5-F   H  O H  H  OCH.sub.3 O(CH.sub.2).sub.2 COOC.sub.2 H.sub.5         ##STR203##                                                                            5-CH.sub.3                                                                           H  O H  CH.sub.3                                                                          OCH.sub.3 OCH.sub.3                                    ##STR204##                                                                            5-F   H  O H  CH.sub.3                                                                          CH.sub.3  OCH.sub.3                                    ##STR205##                                                                            3-Cl  H  O H  CH.sub.3                                                                          OCH.sub.3 N(CH.sub.3).sub.2                            ##STR206##                                                                            5-CH.sub.3                                                                           H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR207##                                                                            5-CN  H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR208##                                                                            5-CF.sub.3                                                                           H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR209##                                                                            5-SO.sub.2 CH.sub.3                                                                  H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR210##                                                                            5-N(CH.sub.3).sub.2                                                                  H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR211##                                                                            5-NH.sub.2                                                                           H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR212##                                                                            H     H  O H  H  OCH.sub.3 SCH.sub.3                                    ##STR213##                                                                            H     H  O H  H  OCH.sub.3 SCH.sub.2 COOCH.sub.3                        ##STR214##                                                                            H     H  O H  H  OCH.sub.3 S(CH.sub.2 ).sub.2 OC.sub.2 H.sub.5          ##STR215##                                                                            4-Cl  5-Cl                                                                              O H  H  OCH.sub.3 OCH.sub.3                                    ##STR216##                                                                            4-F   H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR217##                                                                            4-Cl  5-Cl                                                                              O H  H  OCH.sub.3 CH.sub.3                                     ##STR218##                                                                            4-F   H  O H  H  OCH.sub.3 CH.sub.3                                     ##STR219##                                                                            4-Br  H  O H  H  OCH.sub.3 CH.sub.3                                     ##STR220##                                                                            4-Cl  H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR221##                                                                            H     H  O H  H  CH.sub.3  N(CH.sub.3).sub.2                            ##STR222##                                                                            H     H  O H  H  OCH.sub.3 OCH.sub.2 CF.sub.3                           ##STR223##                                                                            H     H  O H  H  OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.3                 ##STR224##                                                                            H     H  O H  H  OCH.sub.3 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3        ##STR225##                                                                            H     H  O H  H  Cl        Cl                                           ##STR226##                                                                            H     H  O H  H  OCH.sub.2 CH.sub.2 OCH.sub.3                                                             OCH.sub.2 CH.sub.2 OCH.sub.3                 ##STR227##                                                                            H     H  O H  H  OCH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3                  ##STR228##                                                                            H     H  O H  H  CH.sub.3  CH.sub.2 CH.sub.2 OCH.sub.3                  ##STR229##                                                                            H     H  O H  H  CH.sub.3  CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3         ##STR230##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CO.sub.2 CH.sub.3                  ##STR231##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CH.sub.2 OCH.sub.3                 ##STR232##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CF.sub.3                           ##STR233##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3        ##STR234##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CH.sub.3                           ##STR235##                                                                            H     H  O H  H  CH.sub.3                                                                                  ##STR236##                                  ##STR237##                                                                            H     H  O H  H  CH.sub.3  CH.sub.3                                     ##STR238##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR239##                                                                            H     H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR240##                                                                            H     H  O H  H  CH.sub.3  OCH(CH.sub.3).sub.2                          ##STR241##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CH.sub.2 Cl                        ##STR242##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CCl.sub.3                          ##STR243##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CH.sub.2 CN                        ##STR244##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CHCH.sub.2                         ##STR245##                                                                            H     H  O H  H  CH.sub.3  OCH.sub. 2 C CCH.sub.3                       ##STR246##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR247##                                                                            H     H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR248##                                                                            H     H  O H  H  CH.sub.3                                                                                  ##STR249##                                  ##STR250##                                                                            H     H  O H  H  CH.sub.3  CH.sub.3                                     ##STR251##                                                                            H     H  O H  H  CH.sub.3                                                                                  ##STR252##                                  ##STR253##                                                                            H     H  O H  H  CH.sub.3  O(CH.sub.2).sub.2 OC.sub.2 H.sub.5           ##STR254##                                                                            H     H  O H  H  CH.sub.3  SCH.sub.2 CH.sub.2 SCH.sub.3                 ##STR255##                                                                            H     H  O H  H  CH.sub.3                                                                                  ##STR256##                                  ##STR257##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CH.sub.2 SC.sub.2 H.sub.5          ##STR258##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CH.sub.2 SCH.sub.3                 ##STR259##                                                                            H     H  O H  H  CH.sub.3  SCH.sub.2 CH.sub.3                           ##STR260##                                                                            H     H  O H  H  CH.sub.3  SCH.sub.2 CH.sub.2 CN                        ##STR261##                                                                            H     H  O H  H  CH.sub.3  SCH.sub.2 CHCH.sub.2                         ##STR262##                                                                            H     H  O H  H  H         OCH.sub.3                                    ##STR263##                                                                            H     H  O H  H  OCH.sub.3  -n-C.sub.4 H.sub.9                          ##STR264##                                                                            H     H  O H  H  OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3         ##STR265##                                                                            H     H  O H  H  OCH.sub.3 CH.sub.2 CN                                  ##STR266##                                                                            H     H  O H  H  OCH.sub.3 CH.sub.2 CH.sub.2 CN                         ##STR267##                                                                            H     H  O H  H  OCH.sub.3 (CH.sub.2).sub.3 CN                          ##STR268##                                                                            H     H  O H  H  OCH.sub.3 (CH.sub.2).sub.2 CO.sub.2 CH.sub.3           ##STR269##                                                                            H     H  O H  H  OCH.sub.3 CH.sub.2 CH.sub.2 Cl                         ##STR270##                                                                            H     H  O H  H  OCH.sub.3 (CH.sub.2).sub.3 Br                          ##STR271##                                                                            H     H  O H  H  OCH.sub.3 CH.sub.2 CHCHCH.sub.3                        ##STR272##                                                                            H     H  O H  H  OCH.sub.3 CH.sub.2 C CCH.sub.3                         ##STR273##                                                                            H     H  O H  H  OCH.sub.3 NHnC.sub.4 H.sub.9                           ##STR274##                                                                            H     H  O H  H  OCH.sub.3                                                                                 ##STR275##                                  ##STR276##                                                                            H     H  O H  H  OCH.sub.3                                                                                 ##STR277##                                  ##STR278##                                                                            H     H  O H  H  OCH.sub.3                                                                                 ##STR279##                                  ##STR280##                                                                            H     H  O H  H  OCH.sub.3                                                                                 ##STR281##                                  ##STR282##                                                                            H     H  O CH.sub.3                                                                          H  CH.sub.3  OCH.sub.3                                    ##STR283##                                                                            H     H  O CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3  OCH.sub.3                                    ##STR284##                                                                            5-NO.sub.2                                                                           H  O CH.sub.3                                                                          CH.sub.3                                                                          H         OCH.sub.2 CH.sub.2 CO.sub.2 CH.sub.3         ##STR285##                                                                            6-Cl  H  O CH.sub.3                                                                          H  CH.sub.3                                                                                  ##STR286##                                  ##STR287##                                                                            H     H  O CH.sub.3                                                                          CH.sub.3                                                                          OCH.sub.3 N(CH.sub.3).sub.2                            ##STR288##                                                                            H     H  O CH.sub.3                                                                          H  OCH.sub.3 NH(CH.sub.3)                                 ##STR289##                                                                            H     H  O CH.sub.3                                                                          H  OCH.sub.3 CH.sub.3                                     ##STR290##                                                                            H     H  O CH.sub.3                                                                          H  CH.sub.3  CH.sub.3                                     ##STR291##                                                                            H     H  O CH.sub.3                                                                          H  OCH.sub.3 OCH.sub.3                                    ##STR292##                                                                            H     H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR293##                                                                            H     H  O H  H  OCH.sub.3 CH.sub.3                                     ##STR294##                                                                            5-CN  H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR295##                                                                            5-CF.sub.3                                                                           H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR296##                                                                            5-SO.sub.2 CH.sub.3                                                                  H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR297##                                                                            5-OCH.sub.3                                                                          H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR298##                                                                            5-CF.sub.3                                                                           H  O H  H  CH.sub.3  CH.sub.3                                     ##STR299##                                                                            5-Cl  H  O H  H  OCH.sub.3 CH.sub.3                                     ##STR300##                                                                            5-Cl  H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR301##                                                                            H     H  O H  H  OCH.sub.3 OCH.sub.3                                    ##STR302##                                                                            4-Cl  5-Cl                                                                              O H  H  CH.sub.3  CH.sub.3                                     ##STR303##                                                                            H     H  O H  H  CH.sub.3  CH.sub.3                                     ##STR304##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR305##                                                                            5-NO.sub.2                                                                           H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR306##                                                                            5-Cl  H  O H  H  CH.sub.3  OCH.sub.3                                    ##STR307##                                                                            H     H  O H  H  CH.sub.3  OCH.sub.2 CO.sub.2 CH.sub.3                  ##STR308##                                                                            5-CF.sub.3                                                                           H  O H  H  CH.sub.3                                                                                  ##STR309##                                  ##STR310##                                                                            5-CN  H  O H  H  CH.sub.3  OCH.sub.2 CCl.sub.3                          ##STR311##                                                                            5-Cl  6-Cl                                                                              O H  H  CH.sub.3  OCH.sub.2 CHCH.sub.2                         ##STR312##                                                                            5-NO.sub.2                                                                           H  O H  H  CH.sub.3  O(CH.sub.2).sub.2 OCH.sub.3                  ##STR313##                                                                            4-CH.sub.3                                                                           H  O H  H  CH.sub.3  OCH.sub.2 CN                                __________________________________________________________________________

                  TABLE III                                                        ______________________________________                                          ##STR314##                                                                                                         m.p.                                      QR        R.sub.2   R.sub.3                                                                               W   X.sub.1                                                                              Y.sub.1 (°C.)                      ______________________________________                                          ##STR315##                                                                              H         H      O   OCH.sub.3                                                                            CH.sub.3                                   ##STR316##                                                                              H         H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR317##                                                                              6-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR318##                                                                              3-Cl      5-Cl   O   OCH.sub.3                                                                            C.sub.2 H.sub.5                            ##STR319##                                                                              5-OCH.sub.3                                                                              H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR320##                                                                              5-NO.sub.2                                                                               3-Cl   O   OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                         ##STR321##                                                                              5-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR322##                                                                              H         H      O   CH.sub.3                                                                             OC.sub.2 H.sub.5                           ##STR323##                                                                              5-CN      H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR324##                                                                              5-CF.sub.3                                                                               H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR325##                                                                              5-SO.sub.2 CH.sub.3                                                                      H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR326##                                                                              H         H      O   CH.sub.3                                                                             CH.sub.3                                   ##STR327##                                                                              H         H      O   OCH.sub.3                                                                            CH.sub.3                                   ##STR328##                                                                              H         H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR329##                                                                              6-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR330##                                                                              3-Cl      5-Cl   O   OCH.sub.3                                                                            C.sub.2 H.sub.5                            ##STR331##                                                                              5-OCH.sub.3                                                                              H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR332##                                                                              5-NO.sub.2                                                                               3-Cl   O   OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                         ##STR333##                                                                              5-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR334##                                                                              H         H      O   CH.sub.3                                                                             OC.sub.2 H.sub.5                           ##STR335##                                                                              5-CN      H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR336##                                                                              5-CF.sub.3                                                                               H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR337##                                                                              5-SO.sub.2 CH.sub.3                                                                      H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR338##                                                                              H         H      O   CH.sub.3                                                                             CH.sub.3                                   ##STR339##                                                                              H         H      O   OCH.sub.3                                                                            CH.sub.3                                   ##STR340##                                                                              H         H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR341##                                                                              6-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR342##                                                                              3-Cl      5-Cl   O   OCH.sub.3                                                                            C.sub.2 H.sub.5                            ##STR343##                                                                              5-OCH.sub.3                                                                              H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR344##                                                                              5-NO.sub.2                                                                               3-Cl   O   OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                         ##STR345##                                                                              5-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR346##                                                                              H         H      O   CH.sub.3                                                                             OCH.sub.2 H.sub.5                          ##STR347##                                                                              5-CN      H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR348##                                                                              5-CF.sub.3                                                                               H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR349##                                                                              5-SO.sub.2 CH.sub.3                                                                      H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR350##                                                                              H         H      O   CH.sub.3                                                                             CH.sub.3                                   ##STR351##                                                                              H         H      O   CH.sub.3                                                                             CH.sub.3                                   ##STR352##                                                                              5-Cl      H      O   CH.sub.3                                                                             CH.sub.3                                   ##STR353##                                                                              4-NO.sub.2                                                                               H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR354##                                                                              5-SO.sub.2 CH.sub.3                                                                      H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR355##                                                                              5-OCH.sub.3                                                                              H      O   OCH.sub.3                                                                            CH.sub.3                                   ##STR356##                                                                              5-Cl      4-Cl   O   OCH.sub.3                                                                            CH.sub.3                                   ##STR357##                                                                              H         H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR358##                                                                              5-CN      H      O   CH.sub.3                                                                             CH.sub.3                                   ##STR359##                                                                              5-Cl      H      O   CH.sub.3                                                                             OCH.sub.3                                  ##STR360##                                                                              5-NH.sub.2                                                                               H      O   CH.sub.3                                                                             OCH.sub.2 CO.sub.2 CH.sub.3                ##STR361##                                                                              5-CH.sub.3                                                                               H      O   CH.sub.3                                                                             CH.sub.3                                   ##STR362##                                                                              5-SO.sub.2 CH.sub.3                                                                      H      O   OCH.sub.3                                                                            OCH.sub.3                                  ##STR363##                                                                              5-NH.sub.2                                                                               H      O   OCH.sub.3                                                                            CH.sub.2 CO.sub.2 C.sub.2 H.sub.5         ______________________________________                                    

                  TABLE IV                                                         ______________________________________                                          ##STR364##                                                                                                          m.p.                                     QR         R.sub.2   R.sub.3                                                                               W   X.sub.1                                                                              Y.sub.1 (°C.)                     ______________________________________                                          ##STR365##                                                                               H         H      O   OCH.sub.3                                                                            CH.sub.3                                  ##STR366##                                                                               H         H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR367##                                                                               6-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                 ##STR368##                                                                               3-Cl      5-Cl   O   OCH.sub.3                                                                            C.sub.2 H.sub.5                           ##STR369##                                                                               5-OCH.sub.3                                                                              H      O   OCH.sub.3                                                                            OCH.sub.3                                 ##STR370##                                                                               5-NO.sub.2                                                                               3-Cl   O   OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                        ##STR371##                                                                               5-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                 ##STR372##                                                                               H         H      O   CH.sub.3                                                                             OC.sub.2 H.sub.5                          ##STR373##                                                                               5-CN      H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR374##                                                                               5-CF.sub.3                                                                               H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR375##                                                                               5-SO.sub.2 CH.sub.3                                                                      H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR376##                                                                               H         H      O   CH.sub.3                                                                             CH.sub.3                                  ##STR377##                                                                               H         H      O   OCH.sub.3                                                                            CH.sub.3                                  ##STR378##                                                                               H         H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR379##                                                                               6-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                 ##STR380##                                                                               3-Cl      5-Cl   O   OCH.sub.3                                                                            C.sub.2 H.sub.5                           ##STR381##                                                                               5-OCH.sub.3                                                                              H      O   OCH.sub.3                                                                            OCH.sub.3                                 ##STR382##                                                                               5-NO.sub.2                                                                               3-Cl   O   OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                        ##STR383##                                                                               5-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                 ##STR384##                                                                               H         H      O   CH.sub.3                                                                             OC.sub.2 H.sub.5                          ##STR385##                                                                               5-CN      H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR386##                                                                               5-CF.sub.3                                                                               H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR387##                                                                               5-SO.sub.2 CH.sub.3                                                                      H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR388##                                                                               H         H      O   CH.sub.3                                                                             CH.sub.3                                  ##STR389##                                                                               H         H      O   OCH.sub.3                                                                            CH.sub.3                                  ##STR390##                                                                               H         H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR391##                                                                               6-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                 ##STR392##                                                                               3-Cl      5-Cl   O   OCH.sub.3                                                                            C.sub.2 H.sub.5                           ##STR393##                                                                               5-OCH.sub.3                                                                              H      O   OCH.sub.3                                                                            OCH.sub.3                                 ##STR394##                                                                               5-NO.sub.2                                                                               3-Cl   O   OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                        ##STR395##                                                                               5-Cl      H      O   OCH.sub.3                                                                            OCH.sub.3                                 ##STR396##                                                                               H         H      O   CH.sub.3                                                                             OC.sub.2 H.sub.5                          ##STR397##                                                                               5-CN      H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR398##                                                                               5-CF.sub.3                                                                               H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR399##                                                                               5-SO.sub.2 CH.sub.3                                                                      H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR400##                                                                               H         H      O   CH.sub.3                                                                             CH.sub.3                                  ##STR401##                                                                               H         H      O   CH.sub.3                                                                             CH.sub.3                                  ##STR402##                                                                               5-Cl      H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR403##                                                                               5-CF.sub.3                                                                               H      O   CH.sub.3                                                                             OCH.sub.3                                 ##STR404##                                                                               4-Cl      5-Cl   O   OCH.sub.3                                                                            OCH.sub.3                                ______________________________________                                    

                                      TABLE V                                      __________________________________________________________________________      ##STR405##                                                                    R.sub.2        QR  R.sub.3                                                                            R.sub.4                                                                           R.sub.5                                                                           W X       Y        m.p. (°C.)              __________________________________________________________________________     5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.3                                5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.3                               5-NCO          OCH.sub.3                                                                          H   H  H  O OCH.sub.3                                                                              OCH.sub.3                               5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.3                      5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 OCH.sub.3                      5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CO.sub. 2 CH.sub.3            5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR406##                             5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3            5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.3                               5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CH.sub.2 SCH.sub.3            5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CHCH.sub.2                    5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                -n-C.sub.4 H.sub.9                     5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CH.sub.2 CN                    5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CCCH.sub.3                     5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CHCH.sub.2                    5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR407##                             5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               O(CH.sub.2).sub.3 CH.sub.3              5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 Br                   5-NCO          OCH.sub. 3                                                                         H   H  H  O CH.sub.3                                                                               OCH.sub.2 CCl.sub.3                     5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CF.sub.3                                5-NCO          OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                     OCH.sub.2 CH.sub.3                      5-NCO          OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3                                                                               OCH.sub.3                               5-NCO          OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3                                                                               OCH.sub.3                               5-NCO          OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3                                                                               OCH.sub.3                               5-NCO          OCH.sub.3                                                                          3-F H  H  O CH.sub.3                                                                               OCH.sub.3                               5-NCO          OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3                                                                               OCH.sub.3                               5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                               5-NCO          OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                            OCH.sub.3                                ##STR408##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.3 195-198°                 ##STR409##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.3                                                                               184-187°                 ##STR410##    OCH.sub.3                                                                          H   H  H  O OCH.sub.3                                                                              OCH.sub.3                                                                               153-158°                 ##STR411##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.3                       ##STR412##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 OCH.sub.3                       ##STR413##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3              ##STR414##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR415##                              ##STR416##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3             ##STR417##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.3                                ##STR418##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CH.sub.2 SCH.sub.3             ##STR419##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CHCH.sub.2                     ##STR420##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR421##                              ##STR422##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                -n-C.sub.4 H.sub.9                      ##STR423##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CH.sub.2 CN                     ##STR424##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CCCH.sub.3                      ##STR425##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CHCH.sub.2                     ##STR426##    OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                ##STR427##    OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                            OCH.sub.3                                ##STR428##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR429##                              ##STR430##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               O(CH.sub.2).sub.3 CH.sub.3               ##STR431##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 Br                    ##STR432##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CCl.sub.3                      ##STR433##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CF.sub.3                                 ##STR434##    OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                     OCH.sub.2 CH.sub.3                       ##STR435##    OCH.sub.3                                                                          H   H  H  S CH.sub.3                                                                               OCH.sub.3                                ##STR436##    OCH.sub.3                                                                          H   H  H  S OCH.sub.3                                                                              OCH.sub.3                                ##STR437##    OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3                                                                               OCH.sub.3                                ##STR438##    OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3                                                                               OCH.sub.3                                ##STR439##    OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR440##    OCH.sub.3                                                                          3-F H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR441##    OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR442##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.3                                                                               137-140°                 ##STR443##    OCH.sub.3                                                                          H   H  H  O OCH.sub.3                                                                              OCH.sub.3                                                                               186-188°                 ##STR444##    OCH.sub.3                                                                          H   H  H  O OCH.sub.3                                                                              OCH.sub.3                                                                               73-78°                   ##STR445##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.3                                 ##STR446##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR447##    OCH.sub.3                                                                          H   H  H  O OCH.sub.3                                                                              OCH.sub.3                                                                               95-105°                  ##STR448##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.3                       ##STR449##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 OCH.sub.3                       ##STR450##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3              ##STR451##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR452##                              ##STR453##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3             ##STR454##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.3                                ##STR455##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CH.sub.2 SCH.sub.3             ##STR456##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CHCH.sub.2                     ##STR457##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR458##                              ##STR459##    OCH.sub.3                                                                          H   H  H  O CH.sub. 3                                                                               -n-C.sub.4 H.sub.9                      ##STR460##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CH.sub.2 CN                     ##STR461##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CCCH.sub.3                      ##STR462##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CHCH.sub.2                     ##STR463##    OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                ##STR464##    OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                            OCH.sub.3                                ##STR465##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR466##                              ##STR467##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               O(CH.sub.2).sub.3 CH.sub.3               ##STR468##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 Br                    ##STR469##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CCl.sub.3                      ##STR470##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CF.sub.3                                 ##STR471##    OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                     OCH.sub.2 CH.sub.3                       ##STR472##    OCH.sub.3                                                                          H   H  H  S CH.sub.3                                                                               OCH.sub.3                                ##STR473##    OCH.sub.3                                                                          H   H  H  S OCH.sub.3                                                                              OCH.sub.3                                ##STR474##    OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3                                                                               OCH.sub.3                                ##STR475##    OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3                                                                               OCH.sub.3                                ##STR476##    OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR477##    OCH.sub.3                                                                          3-F H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR478##    OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR479##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.3                                 ##STR480##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR481##    OCH.sub.3                                                                          H   H  H  O OCH.sub.3                                                                              OCH.sub.3                                ##STR482##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.3                       ##STR483##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 OCH.sub.3                       ##STR484##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3              ##STR485##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR486##                              ##STR487##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3             ##STR488##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.3                                ##STR489##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CH.sub.2 SCH.sub.3             ##STR490##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CHCH.sub.2                     ##STR491##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR492##                              ##STR493##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                -n-C.sub.4 H.sub.9                      ##STR494##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CH.sub.2 CN                     ##STR495##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CCCH.sub.3                      ##STR496##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CHCH.sub.2                     ##STR497##    OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                     OCH.sub. 3                               ##STR498##    OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                            OCH.sub.3                                ##STR499##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR500##                              ##STR501##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               O(CH.sub.2).sub.3 CH.sub.3               ##STR502##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 Br                    ##STR503##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CCl.sub.3                      ##STR504##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CF.sub.3                                 ##STR505##    OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                     OCH.sub.2 CH.sub.3                       ##STR506##    OCH.sub.3                                                                          H   H  H  S CH.sub.3                                                                               OCH.sub.3                                ##STR507##    OCH.sub.3                                                                          H   H  H  S OCH.sub.3                                                                              OCH.sub.3                                ##STR508##    OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3                                                                               OCH.sub.3                                ##STR509##    OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3                                                                               OCH.sub.3                                ##STR510##    OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR511##    OCH.sub.3                                                                          3-F H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR512##    OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR513##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.3                                 ##STR514##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR515##    OCH.sub.3                                                                          H   H  H  O OCH.sub.3                                                                              OCH.sub.3                                ##STR516##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.3                       ##STR517##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 OCH.sub.3                       ##STR518##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3              ##STR519##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR520##                              ##STR521##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3             ##STR522##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.3                                ##STR523##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CH.sub.2 SCH.sub.3             ##STR524##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CHCH.sub.2                     ##STR525##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR526##                              ##STR527##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                -n-C.sub.4 H.sub.9                      ##STR528##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CH.sub.2 CN                     ##STR529##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CCCH.sub.3                      ##STR530##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CHCH.sub.2                     ##STR531##    OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                ##STR532##    OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                            OCH.sub.3                                ##STR533##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR534##                              ##STR535##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               O(CH.sub.2).sub.3 CH.sub.3               ##STR536##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 Br                    ##STR537##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CCl.sub.3                      ##STR538##    OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CF.sub.3                                 ##STR539##    OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                     OCH.sub.2 CH.sub.3                       ##STR540##    OCH.sub.3                                                                          H   H  H  S CH.sub.3                                                                               OCH.sub.3                                ##STR541##    OCH.sub.3                                                                          H   H  H  S OCH.sub.3                                                                              OCH.sub.3                                ##STR542##    OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3                                                                               OCH.sub.3                                ##STR543##    OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3                                                                               OCH.sub.3                                ##STR544##    OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR545##    OCH.sub.3                                                                          3-F H  H  O CH.sub.3                                                                               OCH.sub.3                                ##STR546##    OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3                                                                               OCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.3                                CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O OCH.sub.3                                                                              OCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.3                      CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 OCH.sub.3                      CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3             CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR547##                             CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3            CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CH.sub.2 SCH.sub.3            CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CHCH.sub.2                    CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR548##                             CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                -n-C.sub.4 H.sub.9                     CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CH.sub.2 CN                    CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CCCH.sub.3                     CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CHCH.sub.2                    CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR549##                             CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               O(CH.sub.2).sub.3 CH.sub.3              CH.sub.3 SO.sub. 2 NH                                                                         OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 Br                   CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CCl.sub.3                     CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CF.sub.3                                CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                     OCH.sub.2 CH.sub.3                      CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  S CH.sub.3                                                                               OCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  S OCH.sub.3                                                                              OCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3                                                                               OCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3                                                                               OCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3                                                                               OCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          3-F H  H  O CH.sub.3                                                                               OCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3                                                                               OCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  H CH.sub.2 OCH.sub. 3                                                                    OCH.sub.3                               CH.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  H CH.sub.2 OCH.sub.2 CH.sub.3                                                            OCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.3                                CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O OCH.sub.3                                                                              OCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.3                      CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 OCH.sub.3                      CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CO.sub.2 CH.sub.3             CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR550##                             CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 OCH.sub.3            CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CH.sub.2 SCH.sub.3            CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               SCH.sub.2 CHCH.sub.2                    CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR551##                             CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                -n-C.sub.4 H.sub.9                     CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CH.sub.2 CN                    CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CH.sub.2 CCCH.sub.3                     CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CHCH.sub.2                    CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                ##STR552##                             CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               O(CH.sub.2).sub.3 CH.sub.3              CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CH.sub.2 Br                   CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               OCH.sub.2 CCl.sub.3                     CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                               CF.sub.3                                CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                     OCH.sub.2 CH.sub.3                      CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  S CH.sub.3                                                                               OCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  S OCH.sub.3                                                                              OCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3                                                                               OCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3                                                                               OCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3                                                                               OCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          3-F H  H  O CH.sub.3                                                                               OCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3                                                                               OCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                               CF.sub.3 SO.sub.2 NH                                                                          OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                            OCH.sub.3                               __________________________________________________________________________

                                      TABLE VI                                     __________________________________________________________________________      ##STR553##                                                                    R.sub.2   QR  R.sub.3                                                                            R.sub.4                                                                           R.sub.5                                                                           W X          Y        m.p. (°C.)                __________________________________________________________________________     5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.3                                  5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.3                                 5-NCO     OCH.sub.3                                                                          H   H  H  O OCH.sub.3  OCH.sub.3                                 5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.3                        5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 OCH.sub.3                        5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CO.sub.2 CH.sub.3               5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR554##                               5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 OCH.sub.3              5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.3                                 5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CH.sub.2 SCH.sub.3              5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CHCH.sub.2                      5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3    -n-C.sub.4 H.sub.9                       5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CH.sub.2 CN                      5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CCCH.sub.3                       5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 CHCH.sub.2             5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR555##                               5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   O(CH.sub.2).sub.3 CH.sub.3                5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 Br                     5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CCl.sub.3                       5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CF.sub.3                                  5-NCO     OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                        OCH.sub.2 CH.sub.3                        5-NCO     OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3   OCH.sub.3                                 5-NCO     OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3   OCH.sub.3                                 5-NCO     OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3   OCH.sub.3                                 5-NCO     OCH.sub.3                                                                          3-F H  H  O CH.sub.3   OCH.sub.3                                 5-NCO     OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3   OCH.sub.3                                 5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                 5-NCO     OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                               OCH.sub.3                                  ##STR556##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.3                                   ##STR557##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.3                                                                               172-175°                   ##STR558##                                                                              OCH.sub.3                                                                          H   H  H  O OCH.sub.3  OCH.sub.3                                  ##STR559##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.3                         ##STR560##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 OCH.sub.3                         ##STR561##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CO.sub.2 CH.sub.3                ##STR562##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR563##                                ##STR564##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 OCH.sub.3               ##STR565##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.3                                  ##STR566##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CH.sub.2 SCH.sub.3               ##STR567##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CHCH.sub.2                       ##STR568##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR569##                                ##STR570##                                                                              OCH.sub. 3                                                                         H   H  H  O CH.sub.3    -n-C.sub.4 H.sub.9                        ##STR571##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CH.sub.2 CN                       ##STR572##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CCCH.sub.3                        ##STR573##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CHCH.sub.2                       ##STR574##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                  ##STR575##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                               OCH.sub.3                                  ##STR576##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR577##                                ##STR578##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   O(CH.sub.2).sub.3 CH.sub.3                 ##STR579##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 Br                      ##STR580##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CCl.sub.3                        ##STR581##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CF.sub.3                                   ##STR582##                                                                              OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                        OCH.sub.2 CH.sub.3                         ##STR583##                                                                              OCH.sub.3                                                                          H   H  H  S CH.sub.3   OCH.sub.3                                  ##STR584##                                                                              OCH.sub.3                                                                          H   H  H  S OCH.sub.3  OCH.sub.3                                  ##STR585##                                                                              OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3   OCH.sub.3                                  ##STR586##                                                                              OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3   OCH.sub.3                                  ##STR587##                                                                              OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3   OCH.sub.3                                  ##STR588##                                                                              OCH.sub.3                                                                          3-F H  H  O CH.sub.3   OCH.sub.3                                  ##STR589##                                                                              OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3   OCH.sub.3                                  ##STR590##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.3                                  ##STR591##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.3                                  ##STR592##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.3                                   ##STR593##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.3                                  ##STR594##                                                                              OCH.sub.3                                                                          H   H  H  O OCH.sub.3  OCH.sub.3                                  ##STR595##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.3                         ##STR596##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 OCH.sub.3                         ##STR597##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CO.sub.2 CH.sub.3                ##STR598##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR599##                                ##STR600##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 OCH.sub.3               ##STR601##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.3                                  ##STR602##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CH.sub.2 SCH.sub.3               ##STR603##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CHCH.sub.2                       ##STR604##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR605##                                ##STR606##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3    -n-C.sub.4 H.sub.9                        ##STR607##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CH.sub.2 CN                       ##STR608##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 C CCH.sub.3                       ##STR609##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CHCH.sub.2                       ##STR610##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                  ##STR611##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                               OCH.sub.3                                  ##STR612##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR613##                                ##STR614##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   O(CH.sub.2).sub.3 CH.sub.3                 ##STR615##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 Br                      ##STR616##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CCl.sub.3                        ##STR617##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CF.sub.3                                   ##STR618##                                                                              OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                        OCH.sub.2 CH.sub.3                         ##STR619##                                                                              OCH.sub.3                                                                          H   H  H  S CH.sub.3   OCH.sub.3                                  ##STR620##                                                                              OCH.sub.3                                                                          H   H  H  S OCH.sub.3  OCH.sub.3                                  ##STR621##                                                                              OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3   OCH.sub.3                                  ##STR622##                                                                              OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3   OCH.sub.3                                  ##STR623##                                                                              OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3   OCH.sub.3                                  ##STR624##                                                                              OCH.sub.3                                                                          3-F H  H  O CH.sub.3   OCH.sub.3                                  ##STR625##                                                                              OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3   OCH.sub.3                                  ##STR626##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.3                                   ##STR627##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.3                                  ##STR628##                                                                              OCH.sub.3                                                                          H   H  H  O OCH.sub.3  OCH.sub.3                                  ##STR629##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.3                         ##STR630##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 OCH.sub.3                         ##STR631##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CO.sub.2 CH.sub.3                ##STR632##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR633##                                ##STR634##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 OCH.sub.3               ##STR635##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.3                                  ##STR636##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CH.sub.2 SCH.sub.3               ##STR637##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CHCH.sub.2                       ##STR638##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR639##                                ##STR640##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3    -n-C.sub.4 H.sub.9                        ##STR641##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CH.sub.2 CN                       ##STR642##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CCCH.sub.3                        ##STR643##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CHCH.sub.2                       ##STR644##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                  ##STR645##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                               OCH.sub.3                                  ##STR646##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR647##                                ##STR648##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   O(CH.sub.2).sub.3 CH.sub.3                 ##STR649##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 Br                      ##STR650##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CCl.sub.3                        ##STR651##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CF.sub.3                                   ##STR652##                                                                              OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                        OCH.sub.2 CH.sub.3                         ##STR653##                                                                              OCH.sub.3                                                                          H   H  H  S CH.sub.3   OCH.sub.3                                  ##STR654##                                                                              OCH.sub.3                                                                          H   H  H  S OCH.sub.3  OCH.sub.3                                  ##STR655##                                                                              OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3   OCH.sub.3                                  ##STR656##                                                                              OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3   OCH.sub.3                                  ##STR657##                                                                              OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3   OCH.sub.3                                  ##STR658##                                                                              OCH.sub.3                                                                          3-F H  H  O CH.sub.3   OCH.sub.3                                  ##STR659##                                                                              OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3   OCH.sub.3                                  ##STR660##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.3                                   ##STR661##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.3                                  ##STR662##                                                                              OCH.sub.3                                                                          H   H  H  O OCH.sub.3  OCH.sub.3                                  ##STR663##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.3                         ##STR664##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 OCH.sub.3                         ##STR665##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CO.sub.2 CH.sub.3                ##STR666##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR667##                                ##STR668##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 OCH.sub.3               ##STR669##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.3                                  ##STR670##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CH.sub.2 SCH.sub.3               ##STR671##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CHCH.sub.2                       ##STR672##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR673##                                ##STR674##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3    -n-C.sub.4 H.sub.9                        ##STR675##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CH.sub.2 CN                       ##STR676##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CCCH.sub.3                        ##STR677##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CHCH.sub.2                       ##STR678##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                  ##STR679##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                               OCH.sub.3                                  ##STR680##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR681##                                ##STR682##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   O(CH.sub.2).sub.3 CH.sub.3                 ##STR683##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 Br                      ##STR684##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CCl.sub.3                        ##STR685##                                                                              OCH.sub.3                                                                          H   H  H  O CH.sub.3   CF.sub.3                                   ##STR686##                                                                              OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                        OCH.sub.2 CH.sub.3                         ##STR687##                                                                              OCH.sub.3                                                                          H   H  H  S CH.sub.3   OCH.sub.3                                  ##STR688##                                                                              OCH.sub.3                                                                          H   H  H  S OCH.sub.3  OCH.sub.3                                  ##STR689##                                                                              OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3   OCH.sub.3                                  ##STR690##                                                                              OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3   OCH.sub.3                                  ##STR691##                                                                              OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3   OCH.sub.3                                  ##STR692##                                                                              OCH.sub.3                                                                          3-F H  H  O CH.sub.3   OCH.sub.3                                  ##STR693##                                                                              OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3   OCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.3                                  CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O OCH.sub.3  OCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 Ch.sub.3                        CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 OCH.sub.3                        CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CO.sub.2 CH.sub.3               CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR694##                               CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 OCH.sub.3              CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CH.sub.2 SCH.sub.3              CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CHCH.sub.2                      CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR695##                               CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3    -n-C.sub.4 H.sub.9                       CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CH.sub.2 CN                      CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CCCH.sub.3                       CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CHCH.sub.2                      CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR696##                               CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   O(CH.sub.2).sub.3 CH.sub.3                CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 Br                     CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CCl.sub.3                       CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CF.sub.3                                  CH.sub.3 SO.sub. 2 NH                                                                    OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                        OCH.sub.2 CH.sub.3                        CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  S CH.sub.3   OCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  S OCH.sub.3  OCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3   OCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3   OCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3   OCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          3-F H  H  O CH.sub.3   OCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3   OCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                 CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                               OCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.3                                  CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O OCH.sub.3  OCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.3                        CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 OCH.sub.3                        CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CO.sub.2 CH.sub.3               CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR697##                               CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 OCH.sub.3              CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CH.sub.2 SCH.sub.3              CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   SCH.sub.2 CHCH.sub.2                      CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR698##                               CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3    -n-C.sub.4 H.sub.9                       CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CH.sub.2 CN                      CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CH.sub.2 CCCH.sub.3                       CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CHCH.sub.2                      CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3                                                                                   ##STR699##                               CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   O(CH.sub.2).sub.3 CH.sub.3                CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CH.sub.2 Br                     CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   OCH.sub.2 CCl.sub.3                       CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.3   CF.sub.3                                  CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O OCH.sub.2 CH.sub.3                                                                        OCH.sub.2 CH.sub.3                        CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  S CH.sub.3   OCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  S OCH.sub.3  OCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  CH.sub.3                                                                          O CH.sub.3   OCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   CH.sub.3                                                                          H  O CH.sub.3   OCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          6-Cl                                                                               H  H  O CH.sub.3   OCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          3-F H  H  O CH.sub.3   OCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          6-CH.sub.3                                                                         H  H  O CH.sub.3   OCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.3                                                                        OCH.sub.3                                 CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                          H   H  H  O CH.sub.2 OCH.sub.2 CH.sub.3                                                               OCH.sub.3                                 __________________________________________________________________________

                  TABLE VII                                                        ______________________________________                                          ##STR700##                                                                    R.sub.2     QR       R.sub.3 W    X.sub.1                                                                               Y.sub.1                               ______________________________________                                         5NCO        OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                              5NCO        OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                             5NCO        OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                              ##STR701## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                               ##STR702## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                              ##STR703## OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                              ##STR704## OCH.sub.3                                                                               H       S    CH.sub.3                                                                              OCH.sub.3                              ##STR705## OCH.sub.3                                                                               6-Cl    O    CH.sub.3                                                                              OCH.sub.3                              ##STR706## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                               ##STR707## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                              ##STR708## OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                              ##STR709## OCH.sub.3                                                                               H       S    CH.sub.3                                                                              OCH.sub.3                              ##STR710## OCH.sub.3                                                                               6-Cl    O    CH.sub.3                                                                              OCH.sub.3                              ##STR711## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                               ##STR712## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                              ##STR713## OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                              ##STR714## OCH.sub.3                                                                               H       S    CH.sub.3                                                                              OCH.sub.3                              ##STR715## OCH.sub. 3                                                                              6-Cl    O    CH.sub.3                                                                              OCH.sub.3                              ##STR716## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                               ##STR717## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                              ##STR718## OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                              ##STR719## OCH.sub.3                                                                               H       S    CH.sub.3                                                                              OCH.sub.3                              ##STR720## OCH.sub.3                                                                               6-Cl    O    CH.sub.3                                                                              OCH.sub.3                             5-CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                              5-CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                             5-CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                             5-CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                               H       S    CH.sub.3                                                                              OCH.sub.3                             5-CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                               6-Cl    O    CH.sub.3                                                                              OCH.sub.3                             ______________________________________                                    

                  TABLE VIII                                                       ______________________________________                                          ##STR721##                                                                    R.sub.2     QR       R.sub.3 W    X.sub.1                                                                               Y.sub.1                               ______________________________________                                         5NCO        OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                              5NCO        OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                             5NCO        OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                              ##STR722## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                               ##STR723## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                              ##STR724## OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                              ##STR725## OCH.sub.3                                                                               H       S    CH.sub.3                                                                              OCH.sub.3                              ##STR726## OCH.sub.3                                                                               6-Cl    O    CH.sub.3                                                                              OCH.sub.3                              ##STR727## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                               ##STR728## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                              ##STR729## OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                              ##STR730## OCH.sub.3                                                                               H       S    CH.sub.3                                                                              OCH.sub.3                              ##STR731## OCH.sub.3                                                                               6-Cl    O    CH.sub.3                                                                              OCH.sub.3                              ##STR732## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                               ##STR733## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                              ##STR734## OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                              ##STR735## OCH.sub.3                                                                               H       S    CH.sub.3                                                                              OCH.sub.3                              ##STR736## OCH.sub. 3                                                                              6-Cl    O    CH.sub.3                                                                              OCH.sub.3                              ##STR737## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                               ##STR738## OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                              ##STR739## OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                              ##STR740## OCH.sub.3                                                                               H       S    CH.sub.3                                                                              OCH.sub.3                              ##STR741## OCH.sub.3                                                                               6-Cl    O    CH.sub.3                                                                              OCH.sub.3                             5-CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                               H       O    CH.sub.3                                                                              CH.sub.3                              5-CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                               H       O    CH.sub.3                                                                              OCH.sub.3                             5-CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                               H       O    OCH.sub.3                                                                             OCH.sub.3                             5-CF.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                               H       S    CH.sub.3                                                                              OCH.sub.3                             5-CH.sub.3 SO.sub.2 NH                                                                     OCH.sub.3                                                                               6-Cl    O    CH.sub.3                                                                              OCH.sub.3                             ______________________________________                                    

                                      TABLE IX                                     __________________________________________________________________________      ##STR742##                                                                    QR        R.sub.2                                                                             R.sub.3                                                                          W R.sub.5                                                                           X       Y                                                __________________________________________________________________________     OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.2 CH.sub.3                                                            CH.sub.3                                         OCH.sub.3 5-Cl H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-NO.sub.2                                                                          H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-OCH.sub.3                                                                         H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-NH.sub.2                                                                          H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-CH.sub.3                                                                          H O H  CH.sub.2 OCH.sub. 3                                                                    OCH.sub.3                                        OCH.sub.3 5-CN H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-Br H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-CF.sub.3                                                                          H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-Cl Cl                                                                               O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 H    H S H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        Oi-C.sub.3 H.sub.7                                                                       H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CH.sub.3                                                                       H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CF.sub.3                                                                       H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR743##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CH.sub.2 Cl                                                                    H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR744##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OC.sub.12 H.sub.25                                                                       H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CHCH.sub.2                                                                     H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CHCCl.sub.2                                                                    H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CH.sub.2 OCH.sub.3                                                             H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR745##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CH.sub.2 SCH.sub.3                                                             H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CCCH.sub.2 Cl                                                                  H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CN                                                                             H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     CH.sub.2 OCH.sub.3                               OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     SCH.sub.3                                        OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.2 CH.sub.2 OCH.sub.3                     OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3             OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     SCH.sub.2 CO.sub.2 CH.sub.3                      OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.2 CF.sub.3                               OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub. 2 CONHCH.sub.3                          OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     Cl                                               OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     n-C.sub.4 H.sub.9                                OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     CH.sub.2 CH.sub.2 CN                             OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                      ##STR746##                                      OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.2 CHCH.sub.2                             OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     CO.sub.2 CH.sub.3                                OCH.sub.3 H    H O CH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        NHCH.sub.3                                                                               H    H O H  CH.sub.2 OCH.sub.3                                                                     CH.sub.3                                         NHCH.sub.3                                                                               H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        N(CH.sub.3).sub.2                                                                        H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR747##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR748##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        NHCH(CH.sub.3).sub.2                                                                     H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        N(CH.sub.3)OCH.sub.3                                                                     H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR749##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR750##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        NHCH.sub.2 CHCH.sub.2                                                                    H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        NHCH.sub.2 CCH                                                                           H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        __________________________________________________________________________

                                      TABLE X                                      __________________________________________________________________________      ##STR751##                                                                    QR        R.sub.2                                                                             R.sub.3                                                                          W R.sub.5                                                                           X       Y                                                __________________________________________________________________________     OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.2 CH.sub.3                                                            CH.sub.3                                         OCH.sub.3 5-Cl H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-NO.sub.2                                                                          H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-OCH.sub.3                                                                         H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-NH.sub.2                                                                          H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-CH.sub.3                                                                          H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-CN H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-Br H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-CF.sub.3                                                                          H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 5-Cl Cl                                                                               O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 H    H S H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        Oi-C.sub.3 H.sub.7                                                                       H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CH.sub.3                                                                       H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CF.sub.3                                                                       H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR752##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CH.sub.2 Cl                                                                    H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR753##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OC.sub.12 H.sub.25                                                                       H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CHCH.sub.2                                                                     H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CHCCl.sub.2                                                                    H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CH.sub.2 OCH.sub.3                                                             H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR754##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CH.sub.2 SCH.sub.3                                                             H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CCCH.sub.2 Cl                                                                  H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.2 CN                                                                             H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     CH.sub.2 OCH.sub.3                               OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     SCH.sub.3                                        OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.2 CH.sub.2 OCH.sub.3                     OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3             OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     SCH.sub.2 CO.sub.2 CH.sub.3                      OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.2 CF.sub.3                               OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.2 CONHCH.sub.3                           OCH.sub.3 H    H O H  CH.sub. 2 OCH.sub.3                                                                    Cl                                               OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     n-C.sub.4 H.sub.9                                OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     CH.sub.2 CH.sub.2 CN                             OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                      ##STR755##                                      OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.2 CHCH.sub.2                             OCH.sub.3 H    H O H  CH.sub.2 OCH.sub.3                                                                     CO.sub.2 CH.sub.3                                OCH.sub.3 H    H O CH.sub.3                                                                          CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        NHCH.sub.3                                                                               H    H O H  CH.sub.2 OCH.sub.3                                                                     CH.sub.3                                         NHCH.sub.3                                                                               H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        N(CH.sub.3).sub.2                                                                        H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR756##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        N(CH.sub.3)CH.sub.2 CH.sub.3                                                             H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR757##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        NHCH(CH.sub.3).sub.2                                                                     H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        N(CH.sub.3)OCH.sub.3                                                                     H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR758##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                         ##STR759##                                                                              H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        NHCH.sub.2 CHCH.sub.2                                                                    H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        NHCH.sub.2 CCH                                                                           H    H O H  CH.sub.2 OCH.sub.3                                                                     OCH.sub.3                                        __________________________________________________________________________

FORMULATIONS

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                  TABLE XI                                                         ______________________________________                                                     Active*                                                                        Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74      1-10                                        Oil Suspensions,                                                                              3-50     40-95      0-15                                        Emulsions, Solu-                                                               tions (including                                                               Eulsifiable                                                                    Concentrates                                                                   Aqueous Suspensions                                                                          10-50     40-84      1-20                                        Dusts          1-25     70-99     0-5                                          Granules and  0.1-95      5-99.9   0-15                                        Pellets                                                                        High-Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                          *Active ingredient plus at least one of a surfactant or a diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, New Jersey. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide", 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, New Jersey, as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp. 147ff and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, February 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, March 14, 1967, Col. 5, line 43 through Col. 1, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182.

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 5, line 66 through Col. 5, line 17 and Examples 1-4.

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc., New York, 1961, pp. 81-96.

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 8 Wettable Powder

    ______________________________________                                         Methyl 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-                                                      80%                                               aminosulfonyl]-5-[(methylamino)carbonylamino]-                                 benzoate                                                                       sodium alkylnaphthalenesulfcnate                                                                            2%                                                sodium ligninsulfonate       2%                                                synthetic amorphous silica   3%                                                kaolinite                    13%                                               ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns and then reblended.

EXAMPLE 9 Wettable Powder

    ______________________________________                                         Methyl 2-[[(4-methoxy-6-methylpyrimidin-2-yl)amino-                                                         50%                                               carbonyl]aminosulfonyl]-5-[(methylamino)-                                      carbonylamino]benzoate                                                         sodium alkylnaphthalenesulfonate                                                                             2%                                               low viscosty methyl cellulose                                                                                2%                                               diatomaceous earth           46%                                               ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles of active essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 10 Granule

    ______________________________________                                         wettable powder of Example 9                                                                              5%                                                  attapulgite granules      95%                                                  (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                              ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 11 Extruded Pellet

    ______________________________________                                         Methyl 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-                                                         25%                                               aminocarbonyl]aminosulfonyl]-5-[(methylamino)-                                 carbonylamino]benzoate                                                         anhydrous sodium sulfate     10%                                               crude calcium ligninsulfonate                                                                                5%                                               sodium alkylnaphthalenesulfonate                                                                             1%                                               calcium/magnesium bentonite  59%                                               ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 12 Oil Suspension

    ______________________________________                                         Methyl 5-[(1,1-dimethylethylamino)carbonylamino]-2-                                                         25%                                               [[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                            aminosulfonyl]benzoate                                                         polyoxyethylene sorbitol hexaoleate                                                                          5%                                               highly aliphatic hydrocarbon oil                                                                            70%                                               ______________________________________                                    

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 13 Wettable Powder

    ______________________________________                                         1-[2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]amino-                                                    20%                                               sulfonyl]benzoyl]-2,3-dihydro-1H--                                             indole                                                                         sodium alkylnaphthalenesulfonate                                                                             4%                                               sodium ligninsulfcnate        4%                                               low viscosity methyl cellulose                                                                               3%                                               attapulgite                  69%                                               ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and shifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 14 Low Strength Granule

    ______________________________________                                         Methyl 5-[(1,1-dimethylethylamino)carbonylamino]-2-                                                          1%                                               [[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino-                                carbonyl]aminosulfonyl]benzoate                                                N,N--dimethylformamide        9%                                               attapulgite granules         90%                                               (U.S.S. 20-40 sieve)                                                           ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules are packaged.

EXAMPLE 15 Aqueous Suspension

    ______________________________________                                         Methyl 5-[(1,1-dimethylethylamino)carbonylamino]-2-                                                         40%                                               [[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                 aminosulfonyl]benzoate                                                         polyacrylic acid thickener   0.3%                                              dodecylphenol polyethylene glycol                                                                           0.5%                                              ether                                                                          disodium phosphate           1%                                                monosodium phosphate         0.5%                                              polyvinyl alcohol            1.0%                                              Water                        56.7%                                             ______________________________________                                    

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 16 Solution

    ______________________________________                                         Methyl 4-[(2-chloroethylamino)carbonylamino]-2-                                                              5%                                               [[(4,6-dimethoxypyrimidin-2-yl)aminosulfonyl]-                                 benzoate, sodium salt                                                          water                        95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 17 Low Strength Granule

    ______________________________________                                         Methyl 4-(acetylamino)-2-[[(4,6-dimethoxy-                                                                 0.1%                                               pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-                                   benzoate                                                                       attapulgite granules       99.9%                                               (U.S.S. 20-40 mesh)                                                            ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 18 Granule

    ______________________________________                                         Methyl 5-[(1-methylethylamino)carbonylamino]-2-[[(4-                                                        80%                                               methoxy-6-methyl-1,3,5-triazin-2-yl)aminosulfonyl]-                            benzoate                                                                       wetting agent                 1%                                               crude ligninsulfonate salt (containing                                                                      10%                                               5-20% cf the natural sugars)                                                   attapulgite clay              9%                                               ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water constant is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE 19 High Strength Concentrate

    ______________________________________                                         Methyl 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                      99%                                              aminosulfonyl]-4-[(methylamino)carbonylamino]-                                 benzoate                                                                       silica aerogel                0.5%                                             synthetic amorphous silica    0.5%                                             ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 20 Wettable Powder

    ______________________________________                                         Methyl 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-                                                         90%                                               aminocarbonyl]aminosulfonyl]-5-[(methylamino)-                                 carbonylamino]benzoate                                                         dioctyl sodium sulfosuccinate                                                                               0.1%                                              synthetic fine silica        9.9%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

EXAMPLE 21 Wettable Powder

    ______________________________________                                         1-[2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                         40%                                               aminosulfonyl]benzoyl]-2,3-dihydro-1H--                                        indole                                                                         sodium ligninsulfonate       20%                                               montmorillonite clay         40%                                               ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and then packaged.

EXAMPLE 22 Oil Suspension

    ______________________________________                                         Methyl 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-                                                      35%                                              aminosulfonyl]-4-[(methylamino)carbonylamino]-                                 benzoate                                                                       blend of polyalcohol carboxylic                                                                               6%                                              esters and oil soluble petroleum                                               sulfonates                                                                     xylene                        59%                                              ______________________________________                                    

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

EXAMPLE 23 Dust

    ______________________________________                                         Methyl 5-[(1,1-dimethylethylamino)carbonylamino]-2-                                                         10%                                               [[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                            aminosulfonyl]benzoate                                                         attapulgite                  10%                                               Pyrophyllite                 80%                                               ______________________________________                                    

The active ingredient is blended with attapulgite and then passed through a hammer mill to produce particles substantially all below 200 microns. The ground concentrate is then blended with powdered pyrophyllite until homogeneous.

UTILITY

The compounds of the present invention are highly active herbicides. They have utility for broad-spectrum pre and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil well sites, drive-in theaters, around billboards, highway and railroad structures. By properly selecting rate and time of application, compounds of this invention may be used also to modify plant growth beneficially.

The precise amount of the compound of Formula I to be used in any given situation will vary according to the particular end result desired, the amount of foliage present, the weeds to be controlled, the soil type, the formulation and mode of application, weather conditions, etc. Since so many variables play a role, it is not possible to state a rate of application suitable for all situations. Broadly speaking, the compounds of this invention are used at levels of about 0.01 to 20 kg/ha with a preferred range of 0.1 to 10 kg/ha. In general, the higher rates of application from within this range will be selected for adverse conditions or where extended persistence in soil is desired.

The compounds of Formula I may be combined with other herbicides and are particularly useful in combination with 3-(3,4-dichlorophenyl)-1,1-dimethyl urea; the triazines such as 2-chloro-4-(ethylamino)-6-(isopropylamino)-s-triazine: the uracils such as 5-bromo-3-sec-butyl-6-methyluracil; N-(phosponomethyl)glycine; 3-cyclohexyl-1-methyl-6-dimethylamino-s-triazine-2,4(1H,3H)-dione; N,N-dimethyl-2,2-diphenylacetamide; 2,4-dichlorophenoxyacetic acid (and closely related compounds); 4-chloro-2-butynyl-3-chlorophenylcarbamate; diisopropylthiolcarbamic acid; ester with 2,3-dichloroallyl alcohol; diisopropylthiolcarbamic acid, S-(2,3,3-trichloroallyl)ester; ethyl-N-benzoyl-N-(3,4-dichlorophenyl)-2-aminopropionate; 1,2-dimethyl-3,5-diphenylpyrazolium methylsulfate; methyl 2-[4-(2,4-dichlorophenoxy)-phenoxy]propanoate; 4-amino-6-tert-butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one; 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea; 3-isopropyl-1H-2,1,3-benzothiodiazin-(4H)-3H-one-2,2-dioxide; α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine; 1,1'-dimethyl-4,4'-bipyridinium ion; monosodium methanearsonate; 2-chloro-2',6'-diethyl(methoxymethyl)acetanilide; and 1,1-dimethyl-3-(α,α,α-trifluoro-m-tolyl)-urea.

The activity of these compounds was discovered in greenhouse tests. The tests are described and the data resulting from them are shown below.

0=no effect

& or 10=maximum effect

C=chlorosis or necrosis

D=defoliation

E=emergence inhibition

G=growth retardation

H=formative effects

U=unusual pigmentation

6Y=adscised buds or flowers

TEST PROCEDURE A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), cassia (Cassia tora), morningglory (Ipomoea spp.), cocklebur (Xanthium spp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated preemergence with a nonphytotoxic solvent solution of the compounds of Table A. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliate leaf expanding, crabgrass with two leaves, barnyardgrass with two leaves, wild oats with two leaves, cassia with three leaves (including cotyledonary ones), morningglory with four leaves (including the cotyledonary ones), cocklebur with four leaves (including the cotyledonary ones), sorghum with four leaves, corn with four leaves, soybean with two cotyledonary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three-five leaves were sprayed with a nonphytotoxic solvent solution of the compounds of Table A. Other containers of the above mentioned weeds and crops were treated pre- or post-emergence with the same nonphytotoxic solvent so as to provide a solvent control. A set of untreated control plants was also included for comparison. Preemergence and postemergence treated plants and controls were maintained in a greenhouse for sixteen days, then all treated plants were compared with their respective controls and rated visually for response to treatment. The data in Table A shows that the compounds of this invention are very effective as herbicides.

    TABLE A       POST-EMERGENCE     MORN-     BARN-         BUSH- COT- ING- COCK- CAS-      NUT- CRAB- YARD- WILD   SOY-  SOR-  kg/ha BEAN TON GLORY LEBUR SIA SEDGE      GRASS GRASS OATS WHEAT CORN BEAN RICE GHUM       ##STR760##       0.05 5C,6Y,9G 4C,4H,8G 4C,9H 4G,5X 1C 1C,9G 4C,8G 5C,9H 6C,9G 4C,9G      3C,8H 1C,5H 9C, 4C,9G       ##STR761##       0.05 6C,6Y,9G 6C,9G 5C,9H 4C,9G 4C,8G 2C,9G 4C,8G 6C,9H 4C,8G 4C,9G      5C,9H 2C,8G 9C 4C,9G       ##STR762##       0.05 1C 1C 2C,6H 0 0 0 0 1C,3H 0 2G 1C,4G 0 1C,5G 2C,8H       ##STR763##       0.05 6Y,4C,4G 7C,4G 8C,6G 4C,5G 7C,6G 0 2G 6C,5G 0 2C 0 6C,5G 3G 6C,7G       ##STR764##       0.05 5C,3G 3C,3G 3G 0 0 0 0 3C,2G 0 0 0 0 3C,2G 2C,5G       ##STR765##       0.05 6Y,5C,6G 6C,5G 10C 5C,4G 10C 0 3C 7C,6G 2C 9C,6G 7C,5G 4C,5G 5C,3G      8C,7G       ##STR766##       0.05 2C,5G 1C,3G 0 0 0 0 2G 3C,3G 0 0 0 0 2C,3G 2C,4G       ##STR767##       0.4 6Y,8D,9G 6C,9G 9C 1C,4G 6C,9G 6C,9G 2C,5G 9C 9C 3C,9G 7U,9C 5C,9G      6C,9G 5U,9C       ##STR768##       0.05 6C,6Y,9G 6C,9G 10C 1C 1C,7G 1C,7G 1C,4G 3G,9H 1C 1C 1C,5H 5C,9G 9C      2C,9H       ##STR769##       0.4 9C 3C,3H,9G 10C 9C 3C,9G 9C 2C,7G 6C,9H 2C 1C 10C 3C,9G 4C,9G      4C,9G   PRE-EMERGENCE     MORN-     BARN-           ING COCK- CAS- NUT-      CRAB- YARD- WILD   SOY-  SOR-  kg/ha   GLORY LEBUR SIA SEDGE GRASS GRASS      OATS WHEAT CORN BEAN RICE GHUM       ##STR770##       0.05   9G 8H 5G 3G 0 3C,6H 4C,9H 9G 3C,9H 2C,4H 4C,8G 6C,9H       ##STR771##       0.05   9G 9H 5C,8G 10E 3C,5G 5C,9H 5C,8G 9H 10H 9H 10E 5C,9H       ##STR772##       0.05   5H 0 0 0 0 0 0 0 0 0 0 0       ##STR773##       0.05   4C,5G 3C,2G 6C,7G 0 2C,3G 7C,6G 4C,5G 2C,3G 4C,5G 5C,3G 7C,6G      5C,7G       ##STR774##       0.05   0 0 0 0 0 0 0 0 0 0 0 0       ##STR775##       0.05   4C,5G 3C,5G 5C,6G 0 2G 2C,3G 4G 2C,5G 2C,3G 3C,3G 4C,5G 6C,7G       ##STR776##       0.05   0 0 0 0 0 0 0 0 0 0 0 0       ##STR777##       0.4   9G -- 9G 10E 2C,8G 3C,9G 1C,8G 1C,9G 1U,9G 9H 10E 9H       ##STR778##       0.05   9G 9H 7G 9G 2C 2C,6H 7G 5G 1C,6G 1C,2G 9H 1C,8G       ##STR779##       0.4   3C,9G 4C,9G 5C,9G 8G 2C,6G 3C,9H 2C,8G 7G 10E 9H 10E 7C,9H 

What is claimed is:
 1. A compound selected from ##STR780## wherein Q is O;R is C₁ -C₁₂ alkyl, C₃ -C₁₀ alkenyl, C₃ -C₁₀ alkynyl, C₂ -C₆ alkyl substituted with one to four substituents selected from 0-3 atoms of F, Cl or Br, 0-2 methoxy groups and 0-1 cyano groups, CH₂ CN, ##STR781## where R₇ ^(') is H or CH₃, C₃ -C₆ alkenyl substituted with 1-3 atoms of F, Cl or Br, C₃ -C₆ alkynyl substituted with one of F, Cl or Br, C₅ -C₈ cycloalkyl, C₅ -C₈ cycloalkenyl, C₅ -C₆ cycloalkyl substituted with OCH₃, alkyl of C₂ -C₄, F, Cl or Br or one to four methyl groups, C₄ -C₁₀ cycloalkylalkyl or C₄ -C₈ cycloalkylalkyl with 1-2 CH₃ ; R is also H, M, CH₂ CH₂ OR₇, CH₂ CH₂ CH₂ OR₇, ##STR782## where R₇ is CH₂ CH₃ or CH(CH₃)₂, CH₂ OR₈ ^(') where R₈ ^(') is CH₃, CH₂ CH₃, CH(CH₃)₂, CH₂ CH₂ OCH₃, or CH₂ CH₂ OCH₂ CH₃, (CH₂ CH₂ O)_(n) ^(') R₈, ##STR783## where R₈ is CH₃, CH₂ CH₃ or CH(CH₃)₂ and n' is ##STR784## where R₁₂ is CH₃, CH₂ CH₃ or CH(CH₃)₂ and provided that R has a total number of carbon atoms ≦13; R₁ is ##STR785## R₂ is NCO, ##STR786## CF₃ SO₂ NH or CH₃ SO₂ NH; B is C₁ -C₄ alkyl optionally substituted with 1-3 atoms of F, Cl, Br or a single OCH₃ group or C₂ -C₄ alkenyl; B^(I) is C₁ -C₄ alkyl or C₃ -C₄ alkenyl; B^(II) is C₁ -C₄ alkyl optionally substituted with CH₂ CH₂ OCH₃, CH₂ CH₂ OCH₂ CH₃ or 1-3 atoms of F, Cl or Br, or C₃ -C₄ alkenyl; B^(III) is C₁ -C₄ alkyl optionally substituted with Cl or OCH₃ or C₃ -C₄ alkenyl; R₃ is H, Cl, Br, F or CH₃ ; R₄ is H or CH₃ ; R₅ is H, CH₃ or OCH₃ ; M is an alkali metal; W is oxygen or sulfur; X is H, Cl, CH₃, OCH₃, OCH₂ CH₃, OCH₂ CH₂ OCH₃, CH₂ OCH₃ or CH₂ OCH₂ CH₃ ; Y is H, F, Cl, Br, C₁ -C₄ alkyl, ##STR787## where L is NH₂, OH, NCH₃, NH(C₁ -C₄ alkyl), N(C₁ -C₄ alkyl)₂ or C₁ -C₆ alkoxy, OCH₃, C₁ -C₄ alkyl substituted with OCH₃, OC₂ H₅, CN or 1 to 3 atoms of F, Cl or Br, C₃ -C₄ alkenyl, CH₂ C.tbd.CR₁₃ where R₁₃ is H, CH₃ or CH₂ Cl, --A--(CH₂)_(n) ^(') --A₁ --(C₁ -C₃ alkyl) where A is 0 or S and A₁ is 0, S or SO₂ and n' is as previously defined, SCN, N₃, NR₁₆ R₁₇ where R₁₆ is H or CH₃ and R₁₇ is H, OCH₃, C₁ -C₆ alkyl, C₁ -C₄ alkyl substituted with CN, C₃ -C₄ alkenyl, C₃ - C₆ cycloalkyl or C₂ -C₃ alkyl substituted with OCH₃ or OC₂ H₅, or R₁₆ and R₁₇ can be taken together to form --CH₂ CH₂ CH₂ CH₂ -- or --CH₂ CH₂ OCH₂ CH₂ --, OR₁₄ where R₁₄ is C₁ -C₄ alkyl substituted with cyano, C₃ -C₄ alkenyl or CH₂ Cσ-- CR₁₃ where R₁₃ is as previously defined, ##STR788## or SR₁₅ where R₁₅ is C₁ -C₄ alkyl; with the provision that when Y is ≧4 carbon atoms, R is ≦4 carbon atoms; when X is Cl, then Y is Cl; and when X and Y are both H, then R is ≦4 carbon atoms; and Z is N or CH.
 2. A compound of claim 1 in which W is O, R₃, R₄ and R₅ are H, R₂ is --NCO, ##STR789## CF₃ SO₂ NH or CH₃ SO₂ NH; and Q is O.
 3. A compound of claim 1 in which W is O; R₃, R₄ and R₅ are H; andQR is ##STR790##
 4. A compound of claim 1 in which W is O; R₃, R₄ and R₅ are H and QR is ##STR791##
 5. A compound of claim 1 in which W is O; R₃, R₄ and R₅ are H; andQR is ##STR792##
 6. A compound of claim 2 in which R₂ is in the 5-position of the benzene ring.
 7. A compound of claim 2 in which R₁ is ##STR793##
 8. A compound of claim 7 in which R₂ is in the 5-position of the benzene ring.
 9. A compound of claim 8 in which R is C₁ -C₄ alkyl, C₃ -C₄ alkenyl; C₂ -C₃ alkyl substituted with Cl; CH₂ CH₂ --O--CH₃, CH₂ CH₃); ##STR794## or CH₂ CH₂ CH₂ --O--CH₃, CH₂ CH₃).
 10. A compound of claim 9 in which X is CH₃, OCH₃ or CH₂ OCH₃.
 11. A compound of claim 10 in which Y is CH₃, CH₃ CH₂, C₁ -C₄ alkoxy or CH₃ S.
 12. A compound of claim 11 in which Y is CH₃, CH₃ O or CH₃ S.
 13. A compound of claim 12 in which R is CH₃.
 14. A compound of claim 12 in which B, B^(I), B^(II) are C₁ -C₄ alkyl and B^(III) is C₁ -C₄ alkyl optionally substituted with an atom of F, Cl or Br.
 15. A compound of claim 14 in which X and Y are independently CH₃ or CH₃ O.
 16. A compound of claim 15 in which R is CH₃.
 17. A compound of claim 16 in which R₂ is ##STR795##
 18. A compound of claim 3 in which R₂ is H, F, Cl, Br, CH₃, CH₃ O or CF₃.
 19. A compound of claim 18 in whichR₁ is ##STR796##
 20. A compound of claim 19 in which X is CH₃, CH₃ O, or CH₂ OCH₃ ; and Y is CH₃, CH₃ O or CH₃ S.
 21. A compound of claim 20 in which R₂ is H; and X and Y are independently CH₃ or CH₃ O.
 22. A compound of claim 21 in which QR is ##STR797##
 23. A compound of claim 5 in which R₂ is H, F, Cl, Br, CH₃, CH₃ O or CF₃.
 24. A compound of claim 23 in which R₁ is ##STR798##
 25. A compound of claim 24 in which X and Y are independently CH₃ or CH₃ O.
 26. A compound of claim 25 in which R₂ is H.
 27. The compound of claim 1, methyl 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-5-[(methylamino)carbonylamino]benzoate.
 28. The compound of claim 1, methyl 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-5-[(methylamino)carbonylamino]benzoate.
 29. The compound of claim 1, methyl 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-5-[(methylamino)carbonylamino]benzoate.
 30. The compound of claim 1, methyl 5-[(1,1-dimethylethylamino)carbonylamino]-2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
 31. The compound of claim 1, methyl 5-[(1,1-dimethylethylamino)carbonylamino]-2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
 32. The compound of claim 1, methyl 5-[(1,1-dimethylethylamino)carbonylamino]-2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
 33. The compound of claim 1, methyl 5-[(1-methylethylamino)carbonylamino]-2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminosulfonyl]benzoate.
 34. The compound of claim 1, methyl 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-4-[(methylamino)carbonylamino]benzoate.
 35. The compound of claim 1, methyl 4-(acetylamino)-2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
 36. The compound of claim 1, methyl 4-[(2-chloroethylamino)carbonylamino]-2-[[(4,6-dimethoxypyrimidin-2-yl)aminosulfonyl]benzoate.
 37. The compound of claim 1, 1-[2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]-2,3-dihydro-1H-indole.
 38. The compound of claim 1, 1-[2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]-2,3-dihydro-1H-indole.
 39. The compound of claim 1, 1-[2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]-2,3-dihydro-1H-indole.
 40. The compound of claim 1, 1-[2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]-2,3-dihydro-1H-indole.
 41. The compound of claim 1, 1-[2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]-2,3-dihydro-1H-indole.
 42. The compound of claim 1, 1-[2-[[4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]-2,3-dihydro-1H-indole.
 43. The compound of claim 1, 2-oxiranylmethyl 2-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
 44. The compound of claim 1, 2-oxiranylmethyl 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
 45. The compound of claim 1, 2-oxiranylmethyl 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
 46. The compound of claim 1, 2-oxiranylmethyl 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoate
 47. The compound of claim 1, 2-oxiranylmethyl 2-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
 48. The compound of claim 1, 2-oxiranylmethyl 2-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
 49. The compound of claim 1, 2-oxiranylmethyl 2-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate.
 50. The compound of claim 1, methyl 2-[[(4-methoxymethyl-6-methylthio-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoate. 